Compound and organic light-emitting device including the same

ABSTRACT

An organic light-emitting device includes: a first electrode; a second electrode facing the first electrode; and an organic layer between the first electrode and the second electrode, the organic layer including an emission layer, wherein the organic layer comprises a compound represented by Formula 1. An organic light-emitting device including the compound may have high efficiency, low voltage, high luminance, and a long lifespan.

CROSS-REFERENCE TO RELATED APPLICATION

This application claims priority to and the benefit of Korean PatentApplication No. 10-2015-0144316, filed on Oct. 15, 2015, in the KoreanIntellectual Property Office, the entire content of which isincorporated herein by reference.

BACKGROUND

1. Field

One or more aspects of embodiments of the present disclosure relate to acompound and an organic light-emitting device including the same.

2. Description of the Related Art

Organic light-emitting devices are self-emission devices that have wideviewing angles, high contrast ratios, short response times, andexcellent brightness, driving voltage, and/or response speedcharacteristics, and can produce full-color images. An organiclight-emitting device may include a first electrode disposed (e.g.,positioned) on a substrate, and a hole transport region, an emissionlayer, an electron transport region, and a second electrode, which aresequentially disposed on the first electrode. Holes provided from thefirst electrode, for example, may move toward the emission layer throughthe hole transport region, and electrons provided from the secondelectrode, for example, may move toward the emission layer through theelectron transport region. Carriers, such as the holes and electrons,can then recombine in the emission layer to produce excitons. Theseexcitons transition from an excited state to a ground state, therebygenerating light.

SUMMARY

One or more aspects of example embodiments of the present disclosure aredirected toward compounds that have excellent electron transportcapability and material stability and that are suitable for use as anelectron injection material or electron transport material.

One or more aspects of example embodiments are directed toward organiclight-emitting devices that have high efficiency, low voltage, highluminance, and long lifespan, due to the inclusion of the compoundsaccording to embodiments of the present disclosure.

Additional aspects will be set forth in part in the description whichfollows and, in part, will be apparent from the description, or may belearned by practice of the presented embodiments.

According to one or more example embodiments, a compound represented byFormula 1 is provided:

In Formula 1,

A₁ to A₈ may each independently be selected from CR₁₁, CR₁₂, CR₁₃, CR₁₄,CR₁₅, CR₁₆, CR₁₇, CR₁₈, and N; where at least one of A₁ to A₈ is N;

R₁, R₂, R₁₁, R₁₂, R₁₃, R₁₄, R₁₅, R₁₆, R₁₇, and R₁₈ may eachindependently be selected from hydrogen, deuterium, a halogen group, anitro group, a cyano group, a substituted or unsubstituted C₁-C₆₀ alkylgroup, a substituted or unsubstituted C₂-C₆₀ alkenyl group, asubstituted or unsubstituted C₂-C₆₀ alkynyl group, a substituted orunsubstituted C₁-C₆₀ alkoxy group, a substituted or unsubstituted C₃-C₁₀cycloalkyl group, a substituted or unsubstituted C₂-C₁₀ heterocycloalkylgroup, a substituted or unsubstituted C₃-C₁₀ cycloalkenyl group, asubstituted or unsubstituted C₂-C₁₀ heterocycloalkenyl group, asubstituted or unsubstituted C₆-C₆₀ aryl group, a substituted orunsubstituted C₆-C₆₀ aryloxy group, a substituted or unsubstitutedC₆-C₆₀ arylthio group, a substituted or unsubstituted C₁-C₆₀ heteroarylgroup, a substituted or unsubstituted monovalent non-aromatic condensedpolycyclic group, a substituted or unsubstituted monovalent non-aromaticcondensed heteropolycyclic group, P(═O)R₃₁R₃₂, P(═S)R₃₃R₃₄, S(═O)₂R₃₅,and S(═O)R₃₆;

R₃₁, R₃₂, R₃₃, R₃₄, R₃₅, and R₃₆ may each independently be selected fromhydrogen, deuterium, a halogen group, a nitro group, a cyano group, asubstituted or unsubstituted C₁-C₆₀ alkyl group, a substituted orunsubstituted C₆-C₆₀ aryl group, a substituted or unsubstituted C₁-C₆₀heteroaryl group, and a substituted or unsubstituted monovalentnon-aromatic condensed polycyclic group;

L₁ and L₂ may each independently be selected from a substituted orunsubstituted C₆-C₆₀ arylene group, a substituted or unsubstitutedC₁-C₆₀ heteroarylene group, a substituted or unsubstituted divalentnon-aromatic condensed polycyclic group, and a substituted orunsubstituted divalent non-aromatic condensed heteropolycyclic group;

a1 and a2 may be each independently an integer selected from 0 to 3;

m and n may each independently be an integer selected from 1 to 2; and

at least one substituent of the substituted C₁-C₆₀ alkyl group,substituted C₂-C₆₀ alkenyl group, substituted C₂-C₆₀ alkynyl group,substituted C₁-C₆₀ alkoxy group, substituted C₃-C₁₀ cycloalkyl group,substituted C₂-C₁₀ heterocycloalkyl group, substituted C₃-C₁₀cycloalkenyl group, substituted C₂-C₁₀ heterocycloalkenyl group,substituted C₆-C₆₀ aryl group, substituted C₆-C₆₀ aryloxy group,substituted C₆-C₆₀ arylthio group, substituted C₁-C₆₀ heteroaryl group,substituted monovalent non-aromatic condensed polycyclic group,substituted monovalent non-aromatic condensed heteropolycyclic group,substituted C₆-C₆₀ arylene group, substituted C₁-C₆₀ heteroarylenegroup, a substituted divalent non-aromatic condensed polycyclic group,and a substituted divalent non-aromatic condensed heteropolycyclic groupmay be selected from the group consisting of:

deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitrogroup, an amino group, an amidino group, a hydrazine group, a hydrazonegroup, a carboxylic acid group or a salt thereof, a sulfonic acid groupor a salt thereof, a phosphoric acid group or a salt thereof, a C₁-C₆₀alkyl group, a C₂-C₆₀ alkenyl group, a C₂-C₆₀ alkynyl group, and aC₁-C₆₀ alkoxy group;

a C₁-C₆₀ alkyl group, a C₂-C₆₀ alkenyl group, a C₂-C₆₀ alkynyl group,and a C₁-C₆₀ alkoxy group, each substituted with at least one selectedfrom deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, anitro group, an amino group, an amidino group, a hydrazine group, ahydrazone group, a carboxylic acid group or a salt thereof, a sulfonicacid group or a salt thereof, a phosphoric acid group or a salt thereof,a C₃-C₁₀ cycloalkyl group, a C₂-C₁₀ heterocycloalkyl group, a C₃-C₁₀cycloalkenyl group, a C₂-C₁₀ heterocycloalkenyl group, a C₆-C₆₀ arylgroup, a C₆-C₆₀ aryloxy group, a C₆-C₆₀ arylthio group, a C₁-C₆₀heteroaryl group, a monovalent non-aromatic condensed polycyclic group,a monovalent non-aromatic condensed heteropolycyclic group,—N(Q₁₁)(Q₁₂), —Si(Q₁₃)(Q₁₄)(Q₁₅), and —B(Q₁₆)(Q₁₇);

a C₃-C₁₀ cycloalkyl group, a C₂-C₁₀ heterocycloalkyl group, a C₃-C₁₀cycloalkenyl group, a C₂-C₁₀ heterocycloalkenyl group, a C₆-C₆₀ arylgroup, a C₆-C₆₀ aryloxy group, a C₆-C₆₀ arylthio group, a C₁-C₆₀heteroaryl group, a monovalent non-aromatic condensed polycyclic group,and a monovalent non-aromatic condensed heteropolycyclic group; and

a C₃-C₁₀ cycloalkyl group, a C₂-C₁₀ heterocycloalkyl group, a C₃-C₁₀cycloalkenyl group, a C₂-C₁₀ heterocycloalkenyl group, a C₆-C₆₀ arylgroup, a C₆-C₆₀ aryloxy group, a C₆-C₆₀ arylthio group, a C₁-C₆₀heteroaryl group, a monovalent non-aromatic condensed polycyclic group,and a monovalent non-aromatic condensed heteropolycyclic group, eachsubstituted with at least one selected from deuterium, —F, —Cl, —Br, —I,a hydroxyl group, a cyano group, a nitro group, an amino group, anamidino group, a hydrazine group, a hydrazone group, a carboxylic acidgroup or a salt thereof, a sulfonic acid group or a salt thereof, aphosphoric acid group or a salt thereof, a C₁-C₆₀ alkyl group, a C₂-C₆₀alkenyl group, a C₂-C₆₀ alkynyl group, a C₁-C₆₀ alkoxy group, a C₃-C₁₀cycloalkyl group, a C₂-C₁₀ heterocycloalkyl group, a C₃-C₁₀ cycloalkenylgroup, a C₂-C₁₀ heterocycloalkenyl group, a C₆-C₆₀ aryl group, a C₆-C₆₀aryloxy group, a C₆-C₆₀ arylthio group, a C₁-C₆₀ heteroaryl group, amonovalent non-aromatic condensed polycyclic group, a monovalentnon-aromatic condensed heteropolycyclic group, —N(Q₂₁)(Q₂₂),—Si(Q₂₃)(Q₂₄)(Q₂₅), and —B(Q₂₆)(Q₂₇),

wherein Q₁₁ to Q₁₇ and Q₂₁ to Q₂₇ may be each independently selectedfrom hydrogen, deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyanogroup, a nitro group, an amino group, an amidino group, a hydrazinegroup, a hydrazone group, a carboxylic acid group or a salt thereof, asulfonic acid group or a salt thereof, a phosphoric acid group or a saltthereof, a C₁-C₆₀ alkyl group, a C₂-C₆₀ alkenyl group, a C₂-C₆₀ alkynylgroup, a C₁-C₆₀ alkoxy group, a C₃-C₁₀ cycloalkyl group, a C₂-C₁₀heterocycloalkyl group, a C₃-C₁₀ cycloalkenyl group, a C₂-C₁₀heterocycloalkenyl group, a C₆-C₆₀ aryl group, a C₁-C₆₀ heteroarylgroup, a monovalent non-aromatic condensed polycyclic group, and amonovalent non-aromatic condensed heteropolycyclic group.

According to one or more example embodiments, an organic light-emittingdevice includes: a first electrode; a second electrode facing the firstelectrode; and an organic layer between the first electrode and thesecond electrode, the organic layer including an emission layer, whereinthe organic layer includes the compound according to embodiments of thepresent disclosure described above.

According to one or more example embodiments, a flat panel displayapparatus includes the organic light-emitting device according toembodiments of the present disclosure, wherein the first electrode ofthe organic light-emitting device is electrically connected (e.g.,coupled) to a source electrode or a drain electrode of a thin filmtransistor.

BRIEF DESCRIPTION OF THE DRAWING

These and/or other aspects will become apparent and more readilyappreciated from the following description of the example embodiments,taken in conjunction with the drawing, which is a schematic view of anorganic light-emitting device according to an embodiment of the presentdisclosure.

DETAILED DESCRIPTION

Reference will now be made in more detail to example embodiments,examples of which are illustrated in the accompanying drawing, whereinlike reference numerals refer to like elements throughout. In thisregard, the present example embodiments may have different forms andshould not be construed as being limited to the descriptions set forthherein. Accordingly, the example embodiments are merely described below,by referring to the drawing, to explain aspects of the presentdescription. As used herein, the term “and/or” includes any and allcombinations of one or more of the associated listed items. Expressionssuch as “at least one of,” “one of,” and “selected from,” when precedinga list of elements, modify the entire list of elements and do not modifythe individual elements of the list. Further, the use of “may” whendescribing embodiments of the present invention refers to one or moreembodiments of the present invention.”

An aspect of embodiments of the present disclosure provides a compoundrepresented by Formula 1:

In Formula 1,

A₁ to A₈ may each independently be selected from CR₁₁, CR₁₂, CR₁₃, CR₁₄,CR₁₅, CR₁₆, CR₁₇, CR₁₈, and N;

where at least one of A₁ to A₈ is N;

R₁, R₂, R₁₁, R₁₂, R₁₃, R₁₄, R₁₅, R₁₆, R₁₇, and R₁₈ may eachindependently be selected from hydrogen, deuterium, a halogen group, anitro group, a cyano group, a substituted or unsubstituted C₁-C₆₀ alkylgroup, a substituted or unsubstituted C₂-C₆₀ alkenyl group, asubstituted or unsubstituted C₂-C₆₀ alkynyl group, a substituted orunsubstituted C₁-C₆₀ alkoxy group, a substituted or unsubstituted C₃-C₁₀cycloalkyl group, a substituted or unsubstituted C₂-C₁₀ heterocycloalkylgroup, a substituted or unsubstituted C₃-C₁₀ cycloalkenyl group, asubstituted or unsubstituted C₂-C₁₀ heterocycloalkenyl group, asubstituted or unsubstituted C₆-C₆₀ aryl group, a substituted orunsubstituted C₆-C₆₀ aryloxy group, a substituted or unsubstitutedC₆-C₆₀ arylthio group, a substituted or unsubstituted C₁-C₆₀ heteroarylgroup, a substituted or unsubstituted monovalent non-aromatic condensedpolycyclic group, a substituted or unsubstituted monovalent non-aromaticcondensed heteropolycyclic group, P(═O)R₃₁R₃₂, P(═S)R₃₃R₃₄, S(═O)₂R₃₅,and S(═O)R₃₆;

R₃₁, R₃₂, R₃₃, R₃₄, R₃₅, and R₃₆ may each independently be selected fromhydrogen, deuterium, a halogen group, a nitro group, a cyano group, asubstituted or unsubstituted C₁-C₆₀ alkyl group, a substituted orunsubstituted C₆-C₆₀ aryl group, a substituted or unsubstituted C₁-C₆₀heteroaryl group, and a substituted or unsubstituted monovalentnon-aromatic condensed polycyclic group;

L₁ and L₂ may each independently be selected from a substituted orunsubstituted C₆-C₆₀ arylene group, a substituted or unsubstitutedC₁-C₆₀ heteroarylene group, a substituted or unsubstituted divalentnon-aromatic condensed polycyclic group, and a substituted orunsubstituted divalent non-aromatic condensed heteropolycyclic group;

a1 and a2 may each independently be an integer selected from 0 to 3;

m and n may each independently be an integer selected from 1 to 2; and

at least one substituent of the substituted C₁-C₆₀ alkyl group,substituted C₂-C₆₀ alkenyl group, substituted C₂-C₆₀ alkynyl group,substituted C₁-C₆₀ alkoxy group, substituted C₃-C₁₀ cycloalkyl group,substituted C₂-C₁₀ heterocycloalkyl group, substituted C₃-C₁₀cycloalkenyl group, substituted C₂-C₁₀ heterocycloalkenyl group,substituted C₆-C₆₀ aryl group, substituted C₆-C₆₀ aryloxy group,substituted C₆-C₆₀ arylthio group, substituted C₁-C₆₀ heteroaryl group,substituted monovalent non-aromatic condensed polycyclic group,substituted monovalent non-aromatic condensed heteropolycyclic group,substituted C₆-C₆₀ arylene group, substituted C₁-C₆₀ heteroarylenegroup, a substituted divalent non-aromatic condensed polycyclic group,and a substituted divalent non-aromatic condensed heteropolycyclic groupmay be selected from the group consisting of:

deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitrogroup, an amino group, an amidino group, a hydrazine group, a hydrazonegroup, a carboxylic acid group or a salt thereof, a sulfonic acid groupor a salt thereof, a phosphoric acid group or a salt thereof, a C₁-C₆₀alkyl group, a C₂-C₆₀ alkenyl group, a C₂-C₆₀ alkynyl group, and aC₁-C₆₀ alkoxy group;

a C₁-C₆₀ alkyl group, a C₂-C₆₀ alkenyl group, a C₂-C₆₀ alkynyl group,and a C₁-C₆₀ alkoxy group, each substituted with at least one selectedfrom deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, anitro group, an amino group, an amidino group, a hydrazine group, ahydrazone group, a carboxylic acid group or a salt thereof, a sulfonicacid group or a salt thereof, a phosphoric acid group or a salt thereof,a C₃-C₁₀ cycloalkyl group, a C₂-C₁₀ heterocycloalkyl group, a C₃-C₁₀cycloalkenyl group, a C₂-C₁₀ heterocycloalkenyl group, a C₆-C₆₀ arylgroup, a C₆-C₆₀ aryloxy group, a C₆-C₆₀ arylthio group, a C₁-C₆₀heteroaryl group, a monovalent non-aromatic condensed polycyclic group,a monovalent non-aromatic condensed heteropolycyclic group,—N(Q₁₁)(Q₁₂), —Si(Q₁₃)(Q₁₄)(Q₁₅), and —B(Q₁₆)(Q₁₇);

a C₃-C₁₀ cycloalkyl group, a C₂-C₁₀ heterocycloalkyl group, a C₃-C₁₀cycloalkenyl group, a C₂-C₁₀ heterocycloalkenyl group, a C₆-C₆₀ arylgroup, a C₆-C₆₀ aryloxy group, a C₆-C₆₀ arylthio group, a C₁-C₆₀heteroaryl group, a monovalent non-aromatic condensed polycyclic group,and a monovalent non-aromatic condensed heteropolycyclic group; and

a C₃-C₁₀ cycloalkyl group, a C₂-C₁₀ heterocycloalkyl group, a C₃-C₁₀cycloalkenyl group, a C₂-C₁₀ heterocycloalkenyl group, a C₆-C₆₀ arylgroup, a C₆-C₆₀ aryloxy group, a C₆-C₆₀ arylthio group, a C₁-C₆₀heteroaryl group, a monovalent non-aromatic condensed polycyclic group,and a monovalent non-aromatic condensed heteropolycyclic group, eachsubstituted with at least one selected from deuterium, —F, —Cl, —Br, —I,a hydroxyl group, a cyano group, a nitro group, an amino group, anamidino group, a hydrazine group, a hydrazone group, a carboxylic acidgroup or a salt thereof, a sulfonic acid group or a salt thereof, aphosphoric acid group or a salt thereof, a C₁-C₆₀ alkyl group, a C₂-C₆₀alkenyl group, a C₂-C₆₀ alkynyl group, a C₁-C₆₀ alkoxy group, a C₃-C₁₀cycloalkyl group, a C₂-C₁₀ heterocycloalkyl group, a C₃-C₁₀ cycloalkenylgroup, a C₂-C₁₀ heterocycloalkenyl group, a C₆-C₆₀ aryl group, a C₆-C₆₀aryloxy group, a C₆-C₆₀ arylthio group, a C₁-C₆₀ heteroaryl group, amonovalent non-aromatic condensed polycyclic group, a monovalentnon-aromatic condensed heteropolycyclic group, —N(Q₂₁)(Q₂₂),—Si(Q₂₃)(Q₂₄)(Q₂₅), and —B(Q₂₆)(Q₂₇),

wherein Q₁₁ to Q₁₇ and Q₂₁ to Q₂₇ may be each independently selectedfrom hydrogen, deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyanogroup, a nitro group, an amino group, an amidino group, a hydrazinegroup, a hydrazone group, a carboxylic acid group or a salt thereof, asulfonic acid group or a salt thereof, a phosphoric acid group or a saltthereof, a C₁-C₆₀ alkyl group, a C₂-C₆₀ alkenyl group, a C₂-C₆₀ alkynylgroup, a C₁-C₆₀ alkoxy group, a C₃-C₁₀ cycloalkyl group, a C₂-C₁₀heterocycloalkyl group, a C₃-C₁₀ cycloalkenyl group, a C₂-C₁₀heterocycloalkenyl group, a C₆-C₆₀ aryl group, a C₁-C₆₀ heteroarylgroup, a monovalent non-aromatic condensed polycyclic group, and amonovalent non-aromatic condensed heteropolycyclic group.

Organometallic complexes including organic single molecular material(s)having relatively high stability to electrons and relatively highelectron mobility may be used as an electron transport material. Forexample, Alq₃ has been described as having high stability and highelectron affinity. However, when Alq₃ is used in a blue emission device,color purity may be decreased due to emission caused by excitondiffusion.

Also, flavon derivatives, germanium, and siliconchloropentadienederivatives have been described. For example, the organic singlemolecular material may include PBD(2-biphenyl-4-yl-5-(4-t-butylphenyl)-1,3,4-oxadiazole)derivativesbinding to a spiro compound and/or TPBI(2,2′,2″-(benzene-1,3,5-triyl)-tris(1-phenyl-1H-benzimidazole) having ahole blocking capability and excellent electron transport capability.For example, benzoimidazole derivatives have been described as havingexcellent durability.

However, an organic light-emitting device including an electrontransport layer using the organic single molecular material may have ashort luminescent lifespan, and low preservation durability andreliability. These problems occur at least in part due to separation orchemical change of an organic material, photochemical or electrochemicalchange of an organic material, and/or oxidation, exfoliation, and lowdurability of a cathode.

The compound of Formula 1 according to an embodiment of the presentdisclosure may be used as an electron transport material for an organiclight-emitting device. The compound of Formula 1 may have high glasstransition temperature (Tg) and a high melting point. Accordingly,during emission, heat resistance to Joule's heat occurring in an organiclayer, between layers constituting the organic layer region, and/orbetween an organic layer and a metal electrode, and resistance tohigh-temperature conditions can be achieved.

An organic light-emitting device manufactured using the compound ofFormula 1 according to an embodiment may have high durability duringpreservation and driving, and, since the compound of Formula 1 includesa heteroatom, characteristics of the organic light-emitting device maybe improved.

In various embodiments, R₁₁, R₁₂, R₁₃, R₁₄, R₁₅, R₁₆, R₁₇, and R₁₈ inFormula 1 may each independently be hydrogen or deuterium.

In various embodiments, R₃₁, R₃₂, R₃₃, R₃₄, R₃₅, and R₃₆ may eachindependently be a substituted or unsubstituted C₆-C₆₀ aryl group.

In various embodiments, L₁ and L₂ in Formula 1 may be each independentlyany one of Formulae 2a to 2d:

In Formulae 2a to 2d, * indicates a binding site.

In various embodiments, R₁ and R₂ in Formula 1 may be each independentlyselected from hydrogen, deuterium, a cyano group, P(═O)R₃₁R₃₂,P(═S)R₃₃R₃₄, and a group represented by one of Formulae 3a to 3k:

In Formulae 3a to 3k, H₁ may be CR₄₁R₄₂, NR₄₃, O, or S,

R₄₁ to R₄₃, Z₁, and Z₂ may be each independently selected from hydrogen,deuterium, a halogen group, a cyano group, a nitro group, a hydroxylgroup, a carboxy group, a substituted or unsubstituted C1 to C20 alkylgroup, a substituted or unsubstituted C6 to 20 aryl group, a substitutedor unsubstituted C1 to C20 heteroaryl group, a substituted orunsubstituted monovalent non-aromatic condensed polycyclic group, and asubstituted or unsubstituted monovalent non-aromatic condensedheteropolycyclic group;

p in Formulae 3a and 3k may be an integer selected from 1 to 4, p inFormula 3c may be an integer selected from 1 to 3, p in Formula 3d maybe an integer selected from 1 to 9, p in Formulae 3e and 3g may be aninteger selected from 1 to 6, p in Formula 3f may be an integer selectedfrom 1 to 5, and p in Formulae 3h, 3i, and 3j may be an integer selectedfrom 1 to 7, where when p is two or more, two or more Z₁(s) may beidentical to or different from each other; and

* indicates a binding site.

In various embodiments, the compound of Formula 1 may be represented byone of Formulae 2 to 5:

The definitions of substituents and symbols of Formulae 2 to 5 may bethe same as described above.

In various embodiments, the compound of Formula 1 may be any one ofCompounds 1 to 113 and 124 to 127, but is not limited thereto:

The term “organic layer” used herein may refer to a single layer and/ora plurality of layers disposed (e.g., positioned) between the firstelectrode and the second electrode of an organic light-emitting device.A material included in the “organic layer” is not limited to an organicmaterial.

The drawing is a schematic view of an organic light-emitting device 10according to an embodiment of the present disclosure. The organiclight-emitting device 10 includes a first electrode 110, an organiclayer 150, and a second electrode 190.

Hereinafter, the structure of an organic light-emitting device accordingto an embodiment and a method of manufacturing an organic light-emittingdevice according to an embodiment will be described in connection withthe drawing.

In the drawing, a substrate may be additionally disposed (e.g.,positioned) under the first electrode 110 or above the second electrode190. The substrate may be a glass substrate and/or a transparent plasticsubstrate, each having excellent mechanical strength, thermal stability,transparency, surface smoothness, ease of handling, and/orwater-resistance.

The first electrode 110 may be formed by depositing or sputtering amaterial for forming the first electrode 110 on the substrate. When thefirst electrode 110 is an anode, the material for forming the firstelectrode 110 may be selected from materials with a high work functionso as to facilitate hole injection. The first electrode 110 may be areflective electrode, a semi-transmissive electrode, or a transmissiveelectrode. The material for the first electrode 110 may be a transparentand/or highly conductive material, and non-limiting examples of suchmaterial include indium tin oxide (ITO), indium zinc oxide (IZO), tinoxide (SnO₂), and zinc oxide (ZnO). When the first electrode 110 is asemi-transmissive electrode or a reflective electrode, at least oneselected from magnesium (Mg), aluminum (Al), aluminum-lithium (Al—Li),calcium (Ca), magnesium-indium (Mg—In), and magnesium-silver (Mg—Ag) maybe used as a material for forming the first electrode 110.

The first electrode 110 may have a single-layer structure, or amulti-layer structure including two or more layers. For example, thefirst electrode 110 may have a three-layered structure of ITO/Ag/ITO,but the structure of the first electrode 110 is not limited thereto.

The organic layer 150 may be disposed on the first electrode 110. Theorganic layer 150 may include an emission layer.

The organic layer 150 may further include a hole transport regiondisposed between the first electrode and the emission layer, and anelectron transport region disposed between the emission layer and thesecond electrode.

In some embodiments, the hole transport region may include at least oneselected from a hole transport layer (HTL), a hole injection layer(HIL), a buffer layer, and an electron blocking layer; and an electrontransport region may include at least one selected from a hole blockinglayer (HBL), an electron transport layer (ETL), and an electroninjection layer (EIL). However, it may be understood that embodiments ofthe present disclosure are not limited thereto.

The hole transport region may have a single-layered structure formed ofa single material, a single-layered structure formed of a plurality ofdifferent materials, or a multi-layered structure having a plurality oflayers formed of a plurality of different materials.

For example, the hole transport region may have a single-layeredstructure formed of a plurality of different materials, or a structureof hole injection layer/hole transport layer, a structure of holeinjection layer/hole transport layer/buffer layer, a structure of holeinjection layer/buffer layer, a structure of hole transport layer/bufferlayer, or a structure of hole injection layer/hole transportlayer/electron blocking layer, wherein the layers of each structure aresequentially stacked from the first electrode 110 in this stated order,but the structure of the hole transport region is not limited thereto.

When the hole transport region includes a hole injection layer, the holeinjection layer may be formed on the first electrode 110 by using one ormore suitable methods such as vacuum deposition, spin coating, casting,a Langmuir-Blodgett (LB) method, ink-jet printing, laser-printing,and/or laser-induced thermal imaging.

When a hole injection layer is formed by vacuum deposition, for example,the vacuum deposition may be performed at a deposition temperature ofabout 100 to about 500° C., at a vacuum degree of about 10⁻⁸ to about10⁻³ torr, and at a deposition rate of about 0.01 to about 100 Å/sec, bytaking into account a compound for forming the hole injection layer tobe deposited, and the structure of the hole injection layer to beformed.

When a hole injection layer is formed by spin coating, for example, thespin coating may be performed at a coating rate of about 2000 rpm toabout 5000 rpm, and at a temperature of about 80° C. to 200° C., bytaking into account a compound for forming the hole injection layer tobe deposited, and the structure of the hole injection layer to beformed.

When the hole transport region includes a hole transport layer, the holetransport layer may be formed on the first electrode 110 or the holeinjection layer by using one or more suitable methods such as vacuumdeposition, spin coating, casting, a LB method, ink-jet printing,laser-printing, and/or laser-induced thermal imaging.

When the hole transport layer is formed by vacuum deposition and/or spincoating, deposition and coating conditions for the hole transport layermay be the same as (or substantially similar to) the deposition andcoating conditions for the hole injection layer.

The hole transport region may include m-MTDATA, TDATA, 2-TNATA, NPB,β-NPB, TPD, Spiro-TPD, Spiro-NPB, methylated NPB, TAPC, HMTPD,4,4′,4″-tris(N-carbazolyl)triphenylamine (TCTA),polyaniline/dodecylbenzenesulfonic acid (Pani/DBSA),poly(3,4-ethylenedioxythiophene)/poly(4-styrenesulfonate) (PEDOT/PSS),polyaniline/camphor sulfonicacid (Pani/CSA),(polyaniline)/poly(4-styrenesulfonate) (PANI/PSS), a compoundrepresented by Formula 201 below, and/or a compound represented byFormula 202 below:

In Formulae 201 and 202,

L₂₀₁ to L₂₀₅ may each independently be selected from a substituted orunsubstituted C₆-C₆₀ arylene group, a substituted or unsubstitutedC₁-C₆₀ heteroarylene group, a substituted or unsubstituted divalentnon-aromatic condensed polycyclic group, and a substituted orunsubstituted divalent non-aromatic condensed heteropolycyclic group;

xa1 to xa4 may each independently be selected from 0, 1, 2, and 3;

xa5 may be selected from 1, 2, 3, 4, and 5; and

R₂₀₁ to R₂₀₄ may each independently be selected from a substituted orunsubstituted C₃-C₁₀ cycloalkyl group, a substituted or unsubstitutedC₂-C₁₀ heterocycloalkyl group, a substituted or unsubstituted C₃-C₁₀cycloalkenyl group, a substituted or unsubstituted C₂-C₁₀heterocycloalkenyl group, a substituted or unsubstituted C₆-C₆₀ arylgroup, a substituted or unsubstituted C₆-C₆₀ aryloxy group, asubstituted or unsubstituted C₆-C₆₀ arythio group, a substituted orunsubstituted C₁-C₆₀ heteroaryl group, a substituted or unsubstitutedmonovalent non-aromatic condensed polycyclic group, and a substituted orunsubstituted monovalent non-aromatic condensed heteropolycyclic group.

In some embodiments, in Formulae 201 and 202,

L₂₀₁ to L₂₀₅ may each independently be selected from the groupconsisting of:

a phenylene group, a naphthylene group, a fluorenylene group, aspiro-fluorenylene group, a benzofluorenylene group, adibenzofluorenylene group, a phenanthrenylene group, an anthracenylenegroup, a pyrenylene group, a chrysenylene group, a pyridinylene group, apyrazinylene group, a pyrimidinylene group, a pyridazinylene group, aquinolinylene group, an isoquinolinylene group, a quinoxalinylene group,a quinazolinylene group, a carbazolylene group, and a triazinylenegroup; and

a phenylene group, a naphthylene group, a fluorenylene group, aspiro-fluorenylene group, a benzofluorenylene group, adibenzofluorenylene group, a phenanthrenylene group, an anthracenylenegroup, a pyrenylene group, a chrysenylene group, a pyridinylene group, apyrazinylene group, a pyrimidinylene group, a pyridazinylene group, aquinolinylene group, an isoquinolinylene group, a quinoxalinylene group,a quinazolinylene group, a carbazolylene group, and a triazinylenegroup, each substituted with at least one selected from deuterium, —F,—Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an aminogroup, an amidino group, a hydrazine group, a hydrazone group, acarboxylic acid group or a salt thereof, a sulfonic acid group or a saltthereof, a phosphoric acid group or a salt thereof, a C₁-C₂₀ alkylgroup, a C₁-C₂₀ alkoxy group, a phenyl group, a biphenyl group, aterphenyl group, a naphthyl group, a fluorenyl group, a spiro-fluorenylgroup, a benzofluorenyl group, a dibenzofluorenyl group, a phenanthrenylgroup, an anthracenyl group, a pyrenyl group, a chrysenyl group, apyridinyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinylgroup, an isoindolyl group, a quinolinyl group, an isoquinolinyl group,a quinoxalinyl group, a quinazolinyl group, a carbazolyl group, and atriazinyl group;

xa1 to xa4 may each independently be 0, 1, or 2;

xa5 may be 1, 2, or 3;

R₂₀₁ to R₂₀₄ may each independently be selected from the groupconsisting of:

a phenyl group, a naphthyl group, a fluorenyl group, a spiro-fluorenylgroup, a benzofluorenyl group, a dibenzofluorenyl group, a phenanthrenylgroup, an anthracenyl group, a pyrenyl group, a chrysenyl group, apyridinyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinylgroup, a quinolinyl group, an isoquinolinyl group, a quinoxalinyl group,a quinazolinyl group, a carbazolyl group, and a triazinyl group; and

a phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, afluorenyl group, a spiro-fluorenyl group, a benzofluorenyl group, adibenzofluorenyl group, a phenanthrenyl group, an anthracenyl group, apyrenyl group, a chrysenyl group, a pyridinyl group, a pyrazinyl group,a pyrimidinyl group, a pyridazinyl group, a quinolinyl group, anisoquinolinyl group, a quinoxalinyl group, a quinazolinyl group, acarbazolyl group, and a triazinyl group, each substituted with at leastone selected from deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyanogroup, a nitro group, an amino group, an amidino group, a hydrazinegroup, a hydrazone group, a carboxylic acid group or a salt thereof, asulfonic acid group or a salt thereof, a phosphoric acid group or a saltthereof, a C₁-C₂₀ alkyl group, a C₁-C₂₀ alkoxy group, a phenyl group, abiphenyl group, a terphenyl group, a naphthyl group, an azulenyl group,a fluorenyl group, a spiro-fluorenyl group, a benzofluorenyl group, adibenzofluorenyl group, a phenanthrenyl group, an anthracenyl group, apyrenyl group, a chrysenyl group, a pyridinyl group, a pyrazinyl group,a pyrimidinyl group, a pyridazinyl group, a quinolinyl group, anisoquinolinyl group, a quinoxalinyl group, a quinazolinyl group, acarbazolyl group, and a triazinyl group, but embodiments of the presentdisclosure are not limited thereto.

The compound represented by Formula 201 may be represented by Formula201A:

For example, the compound represented by Formula 201 may be representedby Formula 201A-1 below, but is not limited thereto:

For example, the compound represented by Formula 202 may be representedby Formula 202A below, but is not limited thereto:

L₂₀₁ to L₂₀₃, xa1 to xa3, xa5, and R₂₀₂ to R₂₀₄ in Formulae 201A, 201A-1and 202A are already described above; the description of R₂₁₁ may beunderstood by referring to the description provided herein in connectionwith R₂₀₃; and R₂₁₃ to R₂₁₆ may each independently be selected fromhydrogen, deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group,a nitro group, an amino group, an amidino group, a hydrazine group, ahydrazone group, a carboxylic acid group or a salt thereof, a sulfonicacid group or a salt thereof, a phosphoric acid group or a salt thereof,a C₁-C₆₀ alkyl group, a C₂-C₆₀ alkenyl group, a C₂-C₆₀ alkynyl group, aC₁-C₆₀ alkoxy group, a C₃-C₁₀ cycloalkyl group, a C₂-C₁₀heterocycloalkyl group, a C₃-C₁₀ cycloalkenyl group, a C₂-C₁₀heterocycloalkenyl group, a C₆-C₆₀ aryl group, a C₆-C₆₀ aryloxy group, aC₆-C₆₀ arylthio group, a C₁-C₆₀ heteroaryl group, a monovalentnon-aromatic condensed polycyclic group, and a monovalent non-aromaticcondensed heteropolycyclic group.

For example, in Formulae 201A, 201A-1, and 202A,

L₂₀₁ to L₂₀₃ may each independently be selected from the groupconsisting of:

a phenylene group, a naphthylene group, a fluorenylene group, aspiro-fluorenylene group, a benzofluorenylene group, adibenzofluorenylene group, a phenanthrenylene group, an anthracenylenegroup, a pyrenylene group, a chrysenylene group, a pyridinylene group, apyrazinylene group, a pyrimidinylene group, a pyridazinylene group, aquinolinylene group, an isoquinolinylene group, a quinoxalinylene group,a quinazolinylene group, a carbazolylene group, and a triazinylenegroup, and

a phenylene group, a naphthylene group, a fluorenylene group, aspiro-fluorenylene group, a benzofluorenylene group, adibenzofluorenylene group, a phenanthrenylene group, an anthracenylenegroup, a pyrenylene group, a chrysenylene group, a pyridinylene group, apyrazinylene group, a pyrimidinylene group, a pyridazinylene group, aquinolinylene group, an isoquinolinylene group, a quinoxalinylene group,a quinazolinylene group, a carbazolylene group, and a triazinylenegroup, each substituted with at least one selected from deuterium, —F,—Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an aminogroup, an amidino group, a hydrazine group, a hydrazone group, acarboxylic acid group or a salt thereof, a sulfonic acid group or a saltthereof, a phosphoric acid group or a salt thereof, a C₁-C₂₀ alkylgroup, a C₁-C₂₀ alkoxy group, a phenyl group, a biphenyl group, aterphenyl group, a naphthyl group, a fluorenyl group, a spiro-fluorenylgroup, a benzofluorenyl group, a dibenzofluorenyl group, a phenanthrenylgroup, an anthracenyl group, a pyrenyl group, a chrysenyl group, apyridinyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinylgroup, a quinolinyl group, an isoquinolinyl group, a quinoxalinyl group,a quinazolinyl group, a carbazolyl group, and a triazinyl group;

xa1 to xa3 may each independently be 0 or 1;

R₂₀₃, R₂₁₁, and R₂₁₂ may each independently be selected from the groupconsisting of:

a phenyl group, a naphthyl group, a fluorenyl group, a spiro-fluorenylgroup, a benzofluorenyl group, a dibenzofluorenyl group, a phenanthrenylgroup, an anthracenyl group, a pyrenyl group, a chrysenyl group, apyridinyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinylgroup, a quinolinyl group, an isoquinolinyl group, a quinoxalinyl group,a quinazolinyl group, a carbazolyl group, and a triazinyl group, and

a phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, afluorenyl group, a spiro-fluorenyl group, a benzofluorenyl group, adibenzofluorenyl group, a phenanthrenyl group, an anthracenyl group, apyrenyl group, a chrysenyl group, a pyridinyl group, a pyrazinyl group,a pyrimidinyl group, a pyridazinyl group, a quinolinyl group, anisoquinolinyl group, a quinoxalinyl group, a quinazolinyl group, acarbazolyl group, and a triazinyl group, each substituted with at leastone selected from deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyanogroup, a nitro group, an amino group, an amidino group, a hydrazinegroup, a hydrazone group, a carboxylic acid group or a salt thereof, asulfonic acid group or a salt thereof, a phosphoric acid group or a saltthereof, a C₁-C₂₀ alkyl group, a C₁-C₂₀ alkoxy group, a phenyl group, abiphenyl group, a terphenyl group, a naphthyl group, a fluorenyl group,a spiro-fluorenyl group, a benzofluorenyl group, a dibenzofluorenylgroup, a phenanthrenyl group, an anthracenyl group, a pyrenyl group, achrysenyl group, a pyridinyl group, a pyrazinyl group, a pyrimidinylgroup, a pyridazinyl group, a quinolinyl group, an isoquinolinyl group,a quinoxalinyl group, a quinazolinyl group, a carbazolyl group, and atriazinyl group;

R₂₁₃ and R₂₁₄ may each independently be selected from the groupconsisting of:

a C₁-C₂₀ alkyl group and a C₁-C₂₀ alkoxy group,

a C₁-C₂₀ alkyl group and a C₁-C₂₀ alkoxy group, each substituted with atleast one selected from deuterium, —F, —Cl, —Br, —I, a hydroxyl group, acyano group, a nitro group, an amino group, an amidino group, ahydrazine group, a hydrazone group, a carboxylic acid group or a saltthereof, a sulfonic acid group or a salt thereof, a phosphoric acidgroup or a salt thereof, a phenyl group, a biphenyl group, a terphenylgroup, a naphthyl group, a fluorenyl group, a spiro-fluorenyl group, abenzofluorenyl group, a dibenzofluorenyl group, a phenanthrenyl group,an anthracenyl group, a pyrenyl group, a chrysenyl group, a pyridinylgroup, a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, aquinolinyl group, an isoquinolinyl group, a quinoxalinyl group, aquinazolinyl group, a carbazolyl group, and a triazinyl group,

a phenyl group, a naphthyl group, a fluorenyl group, a spiro-fluorenylgroup, a benzofluorenyl group, a dibenzofluorenyl group, a phenanthrenylgroup, an anthracenyl group, a pyrenyl group, a chrysenyl group, apyridinyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinylgroup, a quinolinyl group, an isoquinolinyl group, a quinoxalinyl group,a quinazolinyl group, a carbazolyl group, and a triazinyl group, and

a phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, afluorenyl group, a spiro-fluorenyl group, a benzofluorenyl group, adibenzofluorenyl group, a phenanthrenyl group, an anthracenyl group, apyrenyl group, a chrysenyl group, a pyridinyl group, a pyrazinyl group,a pyrimidinyl group, a pyridazinyl group, a quinolinyl group, anisoquinolinyl group, a quinoxalinyl group, a quinazolinyl group, acarbazolyl group, and a triazinyl group, each substituted with at leastone selected from deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyanogroup, a nitro group, an amino group, an amidino group, a hydrazinegroup, a hydrazone group, a carboxylic acid group or a salt thereof, asulfonic acid group or a salt thereof, a phosphoric acid group or a saltthereof, a C₁-C₂₀ alkyl group, a C₁-C₂₀ alkoxy group, a phenyl group, abiphenyl group, a terphenyl group, a naphthyl group, a fluorenyl group,a spiro-fluorenyl group, a benzofluorenyl group, a dibenzofluorenylgroup, a phenanthrenyl group, an anthracenyl group, a pyrenyl group, achrysenyl group, a pyridinyl group, a pyrazinyl group, a pyrimidinylgroup, a pyridazinyl group, a quinolinyl group, an isoquinolinyl group,a quinoxalinyl group, a quinazolinyl group, a carbazolyl group, and atriazinyl group; and

R₂₁₅ and R₂₁₆ may each independently be selected from the groupconsisting of:

hydrogen, deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group,a nitro group, an amino group, an amidino group, a hydrazine group, ahydrazone group, a carboxylic acid group or a salt thereof, a sulfonicacid group or a salt thereof, a phosphoric acid group or a salt thereof,a C₁-C₂₀ alkyl group, and a C₁-C₂₀ alkoxy group,

a C₁-C₂₀ alkyl group and a C₁-C₂₀ alkoxy group, each substituted with atleast one selected from deuterium, —F, —Cl, —Br, —I, a hydroxyl group, acyano group, a nitro group, an amino group, an amidino group, ahydrazine group, a hydrazone group, a carboxylic acid group or a saltthereof, a sulfonic acid group or a salt thereof, a phosphoric acidgroup or a salt thereof, a phenyl group, a biphenyl group, a terphenylgroup, a naphthyl group, a fluorenyl group, a spiro-fluorenyl group, abenzofluorenyl group, a dibenzofluorenyl group, a phenanthrenyl group,an anthracenyl group, a pyrenyl group, a chrysenyl group, a pyridinylgroup, a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, aquinolinyl group, an isoquinolinyl group, a quinoxalinyl group, aquinazolinyl group, a carbazolyl group, and a triazinyl group,

a phenyl group, a naphthyl group, a fluorenyl group, a spiro-fluorenylgroup, a benzofluorenyl group, a dibenzofluorenyl group, a phenanthrenylgroup, an anthracenyl group, a pyrenyl group, a chrysenyl group, apyridinyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinylgroup, a quinolinyl group, an isoquinolinyl group, a quinoxalinyl group,a quinazolinyl group, and a triazinyl group, and

a phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, afluorenyl group, a spiro-fluorenyl group, a benzofluorenyl group, adibenzofluorenyl group, a phenanthrenyl group, an anthracenyl group, apyrenyl group, a chrysenyl group, a pyridinyl group, a pyrazinyl group,a pyrimidinyl group, a pyridazinyl group, a quinolinyl group, anisoquinolinyl group, a quinoxalinyl group, a quinazolinyl group, acarbazolyl group, and a triazinyl group, each substituted with at leastone selected from deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyanogroup, a nitro group, an amino group, an amidino group, a hydrazinegroup, a hydrazone group, a carboxylic acid group or a salt thereof, asulfonic acid group or a salt thereof, a phosphoric acid group or a saltthereof, a C₁-C₂₀ alkyl group, a C₁-C₂₀ alkoxy group, a phenyl group, abiphenyl group, a terphenyl group, a naphthyl group, a fluorenyl group,a spiro-fluorenyl group, a benzofluorenyl group, a dibenzofluorenylgroup, a phenanthrenyl group, an anthracenyl group, a pyrenyl group, achrysenyl group, a pyridinyl group, a pyrazinyl group, a pyrimidinylgroup, a pyridazinyl group, a quinolinyl group, an isoquinolinyl group,a quinoxalinyl group, a quinazolinyl group, a carbazolyl group, and atriazinyl group; and

xa5 may be 1 or 2.

In some embodiments, R₂₁₃ and R₂₁₄ in Formulae 201A and/or 201A-1 may belinked to each other to form a saturated or unsaturated ring.

The compound represented by Formula 201 and the compound represented byFormula 202 may each independently include any of compounds HT1 to HT20illustrated below, but are not limited thereto.

A thickness of the hole transport region may be in a range of about 100Å to about 10,000 Å, for example, about 100 Å to about 1,000 Å. When thehole transport region includes a hole injection layer and a holetransport layer, the thickness of the hole injection layer may be in arange of about 100 Å to about 10,000 Å, for example, about 100 Å toabout 1,000 Å; and the thickness of the hole transport layer may be in arange of about 50 Å to about 2,000 Å, for example, about 100 Å to about1,500 Å. When the thicknesses of the hole transport region, the holeinjection layer and the hole transport layer are within any of theseranges, satisfactory (or suitable) hole transporting characteristics maybe obtained without a substantial increase in driving voltage.

The hole transport region may further include, in addition to thematerials described above, a charge-generation material for theimprovement of conductive properties. The charge-generation material maybe homogeneously or non-homogeneously dispersed in the hole transportregion.

The charge-generation material may be, for example, a p-dopant. Thep-dopant may be one selected from a quinone derivative, a metal oxide,and a cyano group-containing compound, but embodiments are not limitedthereto. Non-limiting examples of the p-dopant include quinonederivatives (such as tetracyanoquinonedimethane (TCNQ) and/or2,3,5,6-tetrafluoro-tetracyano-1,4-benzoquinonedimethane (F4-TCNQ)),metal oxides (such as tungsten oxide and/or molybdenum oxide), andCompound HT-D1 illustrated below.

The hole transport region may further include a buffer layer and/or anelectron blocking layer, in addition to the hole injection layer and thehole transport layer. Since the buffer layer may compensate for anoptical resonance distance according to a wavelength of light emittedfrom the emission layer, light-emission efficiency of the formed organiclight-emitting device may be improved. For use as a material included inthe buffer layer, any of the materials that are included in the holetransport region may be used. The electron blocking layer may functionto prevent or reduce the injection of electrons from the electrontransport region.

An emission layer may be formed on the first electrode 110 or the holetransport region by using one or more suitable methods such as vacuumdeposition, spin coating, casting, a LB method, ink-jet printing,laser-printing, and/or laser-induced thermal imaging. When an emissionlayer is formed by vacuum deposition and/or spin coating, deposition andcoating conditions for the emission layer may be the same as (orsubstantially similar to) those for the hole injection layer.

When the organic light-emitting device 10 is a full color organiclight-emitting device, the emission layer may be patterned into a redemission layer, a green emission layer, and/or a blue emission layer,according to a sub pixel. In some embodiments, the emission layer mayhave a stacked structure of a red emission layer, a green emissionlayer, and a blue emission layer, or may include a red-light emissionmaterial, a green-light emission material, and a blue-light emissionmaterial, which are mixed with each other in a single layer, to emitwhite light.

The emission layer may include a host and a dopant.

For example, the host may include at least one selected from TPBi,TBADN, ADN (herein also referred to as “DNA”), CBP, CDBP, and TCP:

In some embodiments, the host may include a compound represented byFormula 301 below:Ar₃₀₁-[(L₃₀₁)_(xb1)-R³⁰¹]_(xb2).  <Formula 301>

In Formula 301,

Ar₃₀₁ may be selected from the group consisting of:

a naphthalene, a heptalene, a fluorene, a spiro-fluorene, abenzofluorene, a dibenzofluorene, a phenalene, a phenanthrene, ananthracene, a fluoranthene, a triphenylene, a pyrene, a chrysene, anaphthacene, a picene, a perylene, a pentaphene, and anindenoanthracene, and

a naphthalene, a heptalene, a fluorene, a spiro-fluorene, abenzofluorene, a dibenzofluorene, a phenalene, a phenanthrene, ananthracene, a fluoranthene, a triphenylene, a pyrene, a chrysene, anaphthacene, a picene, a perylene, a pentaphene, and anindenoanthracene, each substituted with at least one selected fromdeuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitrogroup, an amino group, an amidino group, a hydrazine group, a hydrazonegroup, a carboxylic acid group or a salt thereof, a sulfonic acid groupor a salt thereof, a phosphoric acid group or a salt thereof, a C₁-C₆₀alkyl group, a C₂-C₆₀ alkenyl group, a C₂-C₆₀ alkynyl group, a C₁-C₆₀alkoxy group, a C₃-C₁₀ cycloalkyl group, a C₂-C₁₀ heterocycloalkylgroup, a C₃-C₁₀ cycloalkenyl group, a C₂-C₁₀ heterocycloalkenyl group, aC₆-C₆₀ aryl group, a C₆-C₆₀ aryloxy group, a C₆-C₆₀ arylthio group, aC₁-C₆₀ heteroaryl group, a monovalent non-aromatic condensed polycyclicgroup, monovalent non-aromatic condensed heteropolycyclic group, and—Si(Q₃₀₁)(Q_(3o2))(Q₃₀₃) (where Q₃₀₁ to Q₃₀₃ may each independently beselected from hydrogen, a C₁-C₆₀ alkyl group, a C₂-C₆₀ alkenyl group, aC₆-C₆₀ aryl group, and a C₁-C₆₀ heteroaryl group);

L₃₀₁ may be selected from a phenylene group, a naphthylene group, afluorenylene group, a spiro-fluorenylene group, a benzofluorenylenegroup, a dibenzofluorenylene group, a phenanthrenylene group, ananthracenylene group, a pyrenylene group, a chrysenylene group, apyridinylene group, a pyrazinylene group, a pyrimidinylene group, apyridazinylene group, a quinolinylene group, an isoquinolinylene group,a quinoxalinylene group, a quinazolinylene group, a carbazolylene group,and a triazinylene group, and

a phenylene group, a naphthylene group, a fluorenylene group, aspiro-fluorenylene group, a benzofluorenylene group, adibenzofluorenylene group, a phenanthrenylene group, an anthracenylenegroup, a pyrenylene group, a chrysenylene group, a pyridinylene group, apyrazinylene group, a pyrimidinylene group, a pyridazinylene group, aquinolinylene group, an isoquinolinylene group, a quinoxalinylene group,a quinazolinylene group, a carbazolylene group, and a triazinylenegroup, each substituted with at least one selected from deuterium, —F,—Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an aminogroup, an amidino group, a hydrazine group, a hydrazone group, acarboxylic acid group or a salt thereof, a sulfonic acid group or a saltthereof, a phosphoric acid group or a salt thereof, a C₁-C₂₀ alkylgroup, a C₁-C₂₀ alkoxy group, a phenyl group, a naphthyl group, afluorenyl group, a spiro-fluorenyl group, a benzofluorenyl group, adibenzofluorenyl group, a phenanthrenyl group, an anthracenyl group, apyrenyl group, a chrysenyl group, a pyridinyl group, a pyrazinyl group,a pyrimidinyl group, a pyridazinyl group, an isoindolyl group, aquinolinyl group, an isoquinolinyl group, a quinoxalinyl group, aquinazolinyl group, a carbazolyl group, and a triazinyl group;

R₃₀₁ may be selected from the group consisting of:

a C₁-C₂₀ alkyl group and a C₁-C₂₀ alkoxy group,

a C₁-C₂₀ alkyl group and a C₁-C₂₀ alkoxy group, each substituted with atleast one selected from deuterium, —F, —Cl, —Br, —I, a hydroxyl group, acyano group, a nitro group, an amino group, an amidino group, ahydrazine group, a hydrazone group, a carboxylic acid group or a saltthereof, a sulfonic acid group or a salt thereof, a phosphoric acidgroup or a salt thereof, a phenyl group, a naphthyl group, a fluorenylgroup, a spiro-fluorenyl group, a benzofluorenyl group, adibenzofluorenyl group, a phenanthrenyl group, an anthracenyl group, apyrenyl group, a chrysenyl group, a pyridinyl group, a pyrazinyl group,a pyrimidinyl group, a pyridazinyl group, a quinolinyl group, anisoquinolinyl group, a quinoxalinyl group, a quinazolinyl group, acarbazolyl group, and a triazinyl group,

a phenyl group, a naphthyl group, a fluorenyl group, a spiro-fluorenylgroup, a benzofluorenyl group, a dibenzofluorenyl group, a phenanthrenylgroup, an anthracenyl group, a pyrenyl group, a chrysenyl group, apyridinyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinylgroup, a quinolinyl group, an isoquinolinyl group, a quinoxalinyl group,a quinazolinyl group, a carbazolyl group, and a triazinyl group, and

a phenyl group, a naphthyl group, a fluorenyl group, a spiro-fluorenylgroup, a benzofluorenyl group, a dibenzofluorenyl group, a phenanthrenylgroup, an anthracenyl group, a pyrenyl group, a chrysenyl group, apyridinyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinylgroup, a quinolinyl group, an isoquinolinyl group, a quinoxalinyl group,a quinazolinyl group, a carbazolyl group, and a triazinyl group, eachsubstituted with at least one selected from deuterium, —F, —Cl, —Br, —I,a hydroxyl group, a cyano group, a nitro group, an amino group, anamidino group, a hydrazine group, a hydrazone group, a carboxylic acidgroup or a salt thereof, a sulfonic acid group or a salt thereof, aphosphoric acid group or a salt thereof, a C₁-C₂₀ alkyl group, a C₁-C₂₀alkoxy group, a phenyl group, a naphthyl group, a fluorenyl group, aspiro-fluorenyl group, a benzofluorenyl group, a dibenzofluorenyl group,a phenanthrenyl group, an anthracenyl group, a pyrenyl group, achrysenyl group, a pyridinyl group, a pyrazinyl group, a pyrimidinylgroup, a pyridazinyl group, a quinolinyl group, an isoquinolinyl group,a quinoxalinyl group, a quinazolinyl group, a carbazolyl group, and atriazinyl group;

xb1 may be selected from 0, 1, 2, and 3; and

xb2 may be selected from 1, 2, 3, and 4.

For example, in Formula 301,

L₃₀₁ may be selected from the group consisting of:

a phenylene group, a naphthylene group, a fluorenylene group, aspiro-fluorenylene group, a benzofluorenylene group, adibenzofluorenylene group, a phenanthrenylene group, an anthracenylenegroup, a pyrenylene group, and a chrysenylene group, and

a phenylene group, a naphthylene group, a fluorenylene group, aspiro-fluorenylene group, a benzofluorenylene group, adibenzofluorenylene group, a phenanthrenylene group, an anthracenylenegroup, a pyrenylene group, and a chrysenylene group, each substitutedwith at least one selected from deuterium, —F, —Cl, —Br, —I, a hydroxylgroup, a cyano group, a nitro group, an amino group, an amidino group, ahydrazine group, a hydrazone group, a carboxylic acid group or a saltthereof, a sulfonic acid group or a salt thereof, a phosphoric acidgroup or a salt thereof, a C₁-C₂₀ alkyl group, a C₁-C₂₀ alkoxy group, aphenyl group, a naphthyl group, a fluorenyl group, a spiro-fluorenylgroup, a benzofluorenyl group, a dibenzofluorenyl group, a phenanthrenylgroup, an anthracenyl group, a pyrenyl group, and a chrysenyl group;

R₃₀₁ may be selected from the group consisting of:

a C₁-C₂₀ alkyl group and a C₁-C₂₀ alkoxy group,

a C₁-C₂₀ alkyl group and a C₁-C₂₀ alkoxy group, each substituted with atleast one selected from deuterium, —F, —Cl, —Br, —I, a hydroxyl group, acyano group, a nitro group, an amino group, an amidino group, ahydrazine group, a hydrazone group, a carboxylic acid group or a saltthereof, a sulfonic acid group or a salt thereof, a phosphoric acidgroup or a salt thereof, a phenyl group, a naphthyl group, a fluorenylgroup, a spiro-fluorenyl group, a benzofluorenyl group, adibenzofluorenyl group, a phenanthrenyl group, an anthracenyl group, apyrenyl group, and a chrysenyl group,

a phenyl group, a naphthyl group, a fluorenyl group, a spiro-fluorenylgroup, a benzofluorenyl group, a dibenzofluorenyl group, a phenanthrenylgroup, an anthracenyl group, a pyrenyl group, and a chrysenyl group, and

a phenyl group, a naphthyl group, a fluorenyl group, a spiro-fluorenylgroup, a benzofluorenyl group, a dibenzofluorenyl group, a phenanthrenylgroup, an anthracenyl group, a pyrenyl group, and a chrysenyl group,each substituted with at least one selected from deuterium, —F, —Cl,—Br, —I, a hydroxyl group, a cyano group, a nitro group, an amino group,an amidino group, a hydrazine group, a hydrazone group, a carboxylicacid group or a salt thereof, a sulfonic acid group or a salt thereof, aphosphoric acid group or a salt thereof, a C₁-C₂₀ alkyl group, a C₁-C₂₀alkoxy group, a phenyl group, a naphthyl group, a fluorenyl group, aspiro-fluorenyl group, a benzofluorenyl group, a dibenzofluorenyl group,a phenanthrenyl group, an anthracenyl group, a pyrenyl group, and achrysenyl group, but embodiments of the present disclosure are notlimited thereto.

For example, the host may include a compound represented by Formula 301Abelow:

Descriptions of substituents of Formula 301A may be understood byreferring to their respective descriptions provided herein.

The compound represented by Formula 301 may include at least one ofCompounds H1 to H42, but is not limited thereto:

In some embodiments, the host may include at least one of Compounds H43to H49 below, but is not limited thereto:

The dopant may include any suitable fluorescent dopant and/orphosphorescent dopant.

The phosphorescent dopant may include an organometallic complexrepresented by Formula 401 below:

In Formula 401,

M may be selected from iridium (Ir), platinum (Pt), osmium (Os),titanium (Ti), zirconium (Zr), hafnium (Hf), europium (Eu), terbium(Tb), and thulium (Tm);

X₄₀₁ to X₄₀₄ may each independently be nitrogen or carbon;

A₄₀₁ and A₄₀₂ rings may each independently be selected from asubstituted or unsubstituted benzene, a substituted or unsubstitutednaphthalene, a substituted or unsubstituted fluorene, a substituted orunsubstituted spiro-fluorene, a substituted or unsubstituted indene, asubstituted or unsubstituted pyrrole, a substituted or unsubstitutedthiophene, a substituted or unsubstituted furan, a substituted orunsubstituted imidazole, a substituted or unsubstituted pyrazole, asubstituted or unsubstituted thiazole, a substituted or unsubstitutedisothiazole, a substituted or unsubstituted oxazole, a substituted orunsubstituted isoxazole, a substituted or unsubstituted pyridine, asubstituted or unsubstituted pyrazine, a substituted or unsubstitutedpyrimidine, a substituted or unsubstituted pyridazine, a substituted orunsubstituted quinoline, a substituted or unsubstituted isoquinoline, asubstituted or unsubstituted benzoquinoline, a substituted orunsubstituted quinoxaline, a substituted or unsubstituted quinazoline, asubstituted or unsubstituted carbazole, a substituted or unsubstitutedbenzoimidazole, a substituted or unsubstituted benzofuran, a substitutedor unsubstituted benzothiophene, a substituted or unsubstitutedisobenzothiophene, a substituted or unsubstituted benzoxazole, asubstituted or unsubstituted isobenzoxazole, a substituted orunsubstituted triazole, a substituted or unsubstituted oxadiazole, asubstituted or unsubstituted triazine, a substituted or unsubstituteddibenzofuran, and a substituted or unsubstituted dibenzothiophene; and

at least one substituent of the substituted benzene, substitutednaphthalene, substituted fluorene, substituted spiro-fluorene,substituted indene, substituted pyrrole, substituted thiophene,substituted furan, substituted imidazole, substituted pyrazole,substituted thiazole, substituted isothiazole, substituted oxazole,substituted isoxazole, substituted pyridine, substituted pyrazine,substituted pyrimidine, substituted pyridazine, substituted quinoline,substituted isoquinoline, substituted benzoquinoline, substitutedquinoxaline, substituted quinazoline, substituted carbazol, substitutedbenzoimidazole, substituted benzofuran, substituted benzothiophene,substituted isobenzothiophene, substituted benzoxazole, substitutedisobenzoxazole, substituted triazole, substituted oxadiazole,substituted triazine, substituted dibenzofuran, and substituteddibenzothiophene may be selected from the group consisting of:

deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitrogroup, an amino group, an amidino group, a hydrazine group, a hydrazonegroup, a carboxylic acid group or a salt thereof, a sulfonic acid groupor a salt thereof, a phosphoric acid group or a salt thereof, a C₁-C₆₀alkyl group, a C₂-C₆₀ alkenyl group, a C₂-C₆₀ alkynyl group, and aC₁-C₆₀ alkoxy group,

a C₁-C₆₀ alkyl group, a C₂-C₆₀ alkenyl group, a C₂-C₆₀ alkynyl group,and a C₁-C₆₀ alkoxy group, each substituted with at least one selectedfrom deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, anitro group, an amino group, an amidino group, a hydrazine group, ahydrazone group, a carboxylic acid group or a salt thereof, a sulfonicacid group or a salt thereof, a phosphoric acid group or a salt thereof,a C₃-C₁₀ cycloalkyl group, a C₂-C₁₀ heterocycloalkyl group, a C₃-C₁₀cycloalkenyl group, a C₂-C₁₀ heterocycloalkenyl group, a C₆-C₆₀ arylgroup, a C₆-C₆₀ aryloxy group, a C₆-C₆₀ arylthio group, a C₁-C₆₀heteroaryl group, a monovalent non-aromatic condensed polycyclic group,a monovalent non-aromatic condensed heteropolycyclic group,—N(Q₄₀₁)(Q₄₀₂), —Si(Q₄₀₃)(Q₄₀₄)(Q₄₀₅), and —B(Q₄₀₆)(Q₄₀₇),

a C₃-C₁₀ cycloalkyl group, a C₂-C₁₀ heterocycloalkyl group, a C₃-C₁₀cycloalkenyl group, a C₂-C₁₀ heterocycloalkenyl group, a C₆-C₆₀ arylgroup, a C₆-C₆₀ aryloxy group, a C₆-C₆₀ arylthio group, a C₁-C₆₀heteroaryl group, and a non-aromatic condensed polycyclic group,

a C₃-C₁₀ cycloalkyl group, a C₂-C₁₀ heterocycloalkyl group, a C₃-C₁₀cycloalkenyl group, a C₂-C₁₀ heterocycloalkenyl group, a C₆-C₆₀ arylgroup, a C₆-C₆₀ aryloxy group, a C₆-C₆₀ arylthio group, a C₁-C₆₀heteroaryl group, a monovalent non-aromatic condensed polycyclic group,and a monovalent non-aromatic condensed heteropolycyclic group, eachsubstituted with at least one selected from deuterium, —F, —Cl, —Br, —I,a hydroxyl group, a cyano group, a nitro group, an amino group, anamidino group, a hydrazine group, a hydrazone group, a carboxylic acidgroup or a salt thereof, a sulfonic acid group or a salt thereof, aphosphoric acid group or a salt thereof, a C₁-C₆₀ alkyl group, a C₂-C₆₀alkenyl group, a C₂-C₆₀ alkynyl group, a C₁-C₆₀ alkoxy group, a C₃-C₁₀cycloalkyl group, a C₂-C₁₀ heterocycloalkyl group, a C₃-C₁₀ cycloalkenylgroup, a C₂-C₁₀ heterocycloalkenyl group, a C₆-C₆₀ aryl group, a C₆-C₆₀aryloxy group, a C₆-C₆₀ arylthio group, a C₁-C₆₀ heteroaryl group, amonovalent non-aromatic condensed polycyclic group, a monovalentnon-aromatic condensed heteropolycyclic group, —N(Q₄₁₁)(Q₄₁₂),—Si(Q₄₁₃)(Q₄₁₄)(Q₄₁₅) and —B(Q₄₁₆)(Q₄₁₇), and

—N(Q₄₂₁)(Q₄₂₂), −Si(Q₄₂₃)(Q₄₂₄)(Q₄₂₅), and —B(Q₄₂₆)(Q₄₂₇),

wherein Q₄₀₁ to Q₄₀₇, Q₄₁₁ to Q₄₁₇ and Q₄₂₁ to Q₄₂₇ may eachindependently be selected from hydrogen, deuterium, —F, —Cl, —Br, —I, ahydroxyl group, a cyano group, a nitro group, an amino group, an amidinogroup, a hydrazine group, a hydrazone group, a carboxylic acid group ora salt thereof, a sulfonic acid group or a salt thereof, a phosphoricacid group or a salt thereof, a C₁-C₆₀ alkyl group, a C₂-C₆₀ alkenylgroup, a C₂-C₆₀ alkynyl group, a C₁-C₆₀ alkoxy group, a C₃-C₁₀cycloalkyl group, a C₂-C₁₀ heterocycloalkyl group, a C₃-C₁₀ cycloalkenylgroup, a C₂-C₁₀ heterocycloalkenyl group, a C₆-C₆₀ aryl group, a C₁-C₆₀heteroaryl group, a monovalent non-aromatic condensed polycyclic group,and a monovalent non-aromatic condensed heteropolycyclic group;

L₄₀₁ may be an organic ligand;

xc1 may be 1, 2, or 3; and

xc2 may be 0, 1, 2, or 3.

In Formula 401, L₄₀₁ may be a monovalent, divalent, or trivalent organicligand. For example, L₄₀₁ may be selected from a halogen ligand (e.g.,Cl and/or F), a diketone ligand (e.g., acetylacetonate,1,3-diphenyl-1,3-propanedionate, 2,2,6,6-tetramethyl-3,5-heptanedionate,and/or hexafluoroacetonate), a carboxylic acid ligand (e.g., picolinate,dimethyl-3-pyrazolecarboxylate, and/or benzoate), a carbon monooxideligand, an isonitrile ligand, a cyano ligand, and a phosphorous ligand(e.g., phosphine and/or phosphite), but is not limited thereto.

When A₄₀₁ in Formula 401 has two or more substituents, the plurality ofsubstituents of A₄₀₁ may be linked to form a saturated or unsaturatedring.

When A₄₀₁ in Formula 402 has two or more substituents, the plurality ofsubstituents of A₄₀₂ may be linked to form a saturated or unsaturatedring.

When xc1 in Formula 401 is two or more, a plurality of ligands inFormula 401 may be identical to or different from each other. When xc1in Formula 401 is two or more, A₄₀₁ and A₄₀₂ of one ligand may eachindependently be respectively connected to A₄₀₁ and A₄₀₂ of otherneighboring ligands, either directly (e.g., via a bond such as a singlebond) or with a linker (e.g., a C₁-C₅ alkylene, —N(R′)— (where R′ may bea C₁-C₁₀ alkyl group or a C₆-C₂₀ aryl group), and/or —C(═O)—)therebetween.

The phosphorescent dopant may include at least one of Compounds PD1 toPD74 below, but is not limited thereto:

In some embodiments, the phosphorescent dopant may include PtOEP:

The fluorescent dopant may include at least one selected from DPVBi,DPAVBi, TBPe, DCM, DCJTB, Coumarin 6, and C545T.

In some embodiments, the fluorescent dopant may include a compoundrepresented by Formula 501 below.

In Formula 501,

Ar₅₀₁ may be selected from the group consisting of:

a naphthalene, a heptalene, a fluorene, a spiro-fluorene, abenzofluorene, a dibenzofluorene, a phenalene, a phenanthrene, ananthracene, a fluoranthene, a triphenylene, a pyrene, a chrysene, anaphthacene, a picene, a perylene, a pentaphene, and anindenoanthracene, and

a naphthalene, a heptalene, a fluorene, a spiro-fluorene, abenzofluorene, a dibenzofluorene, a phenalene, a phenanthrene, ananthracene, a fluoranthene, a triphenylene, a pyrene, a chrysene, anaphthacene, a picene, a perylene, a pentaphene, and anindenoanthracene, each substituted with at least one selected fromdeuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitrogroup, an amino group, an amidino group, a hydrazine group, a hydrazonegroup, a carboxylic acid group or a salt thereof, a sulfonic acid groupor a salt thereof, a phosphoric acid group or a salt thereof, a C₁-C₆₀alkyl group, a C₂-C₆₀ alkenyl group, a C₂-C₆₀ alkynyl group, a C₁-C₆₀alkoxy group, a C₃-C₁₀ cycloalkyl group, a C₂-C₁₀ heterocycloalkylgroup, a C₃-C₁₀ cycloalkenyl group, a C₂-C₁₀ heterocycloalkenyl group, aC₆-C₆₀ aryl group, a C₆-C₆₀ aryloxy group, a C₆-C₆₀ arylthio group, aC₁-C₆₀ heteroaryl group, a monovalent non-aromatic condensed polycyclicgroup, monovalent non-aromatic condensed heteropolycyclic group, and—Si(Q₅₀₁)(Q₅₀₂)(Q₅₀₃) (where Q₅₀₁ to Q₅₀₃ may each independently beselected from hydrogen, a C₁-C₆₀ alkyl group, a C₂-C₆₀ alkenyl group, aC₆-C₆₀ aryl group, and a C₁-C₆₀ heteroaryl group);

descriptions of L₅₀₁ to L₅₀₃ may each independently be the same as thedescription provided herein in connection with L₂₀₃;

R₅₀₁ and R₅₀₂ may each independently be selected from the groupconsisting of:

a phenyl group, a naphthyl group, a fluorenyl group, a spiro-fluorenylgroup, a benzofluorenyl group, a dibenzofluorenyl group, a phenanthrenylgroup, an anthracenyl group, a pyrenyl group, a chrysenyl group, apyridinyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinylgroup, a quinolinyl group, an isoquinolinyl group, a quinoxalinyl group,a quinazolinyl group, a carbazolyl group, a triazinyl group, adibenzofuranyl group, and a dibenzothiophenyl group, and

a phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, afluorenyl group, a spiro-fluorenyl group, a benzofluorenyl group, adibenzofluorenyl group, a phenanthrenyl group, an anthracenyl group, apyrenyl group, a chrysenyl group, a pyridinyl group, a pyrazinyl group,a pyrimidinyl group, a pyridazinyl group, a quinolinyl group, anisoquinolinyl group, a quinoxalinyl group, a quinazolinyl group, acarbazolyl group, a triazinyl group, a dibenzofuranyl group, and adibenzothiophenyl group, each substituted with at least one selectedfrom deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, anitro group, an amino group, an amidino group, a hydrazine group, ahydrazone group, a carboxylic acid group or a salt thereof, a sulfonicacid group or a salt thereof, a phosphoric acid group or a salt thereof,a C₁-C₂₀ alkyl group, a C₁-C₂₀ alkoxy group, a phenyl group, a biphenylgroup, a terphenyl group, a naphthyl group, a fluorenyl group, aspiro-fluorenyl group, a benzofluorenyl group, a dibenzofluorenyl group,a phenanthrenyl group, an anthracenyl group, a pyrenyl group, achrysenyl group, a pyridinyl group, a pyrazinyl group, a pyrimidinylgroup, a pyridazinyl group, a quinolinyl group, an isoquinolinyl group,a quinoxalinyl group, a quinazolinyl group, a carbazolyl group, atriazinyl group, a dibenzofuranyl group, and a dibenzothiophenyl group;

xd1 to xd3 may each independently be selected from 0, 1, 2, and 3; and

xb4 may be selected from 1, 2, 3, and 4.

For example, the fluorescent dopant may include at least one ofCompounds FD1 to FD8:

An amount of the dopant in the emission layer may be, for example, in arange of about 0.01 to about 15 parts by weight based on 100 parts byweight of the host, but is not limited thereto.

A thickness of the emission layer may be in a range of about 100 Å toabout 1,000 Å, for example, about 200 Å to about 600 Å. When thethickness of the emission layer is within any of these ranges, excellent(or suitable) light-emission characteristics may be obtained without asubstantial increase in driving voltage.

An electron transport region may be disposed on the emission layer.

The electron transport region may include at least one selected from ahole blocking layer, an electron transport layer (ETL), and an electroninjection layer, but is not limited thereto.

In some embodiments, the electron transport region may include thecompound of Formula 1 according to an embodiment of the presentdisclosure.

When the electron transport region includes a hole blocking layer, thehole blocking layer may be formed on the emission layer by using one ormore suitable methods such as vacuum deposition, spin coating, casting,a Langmuir-Blodgett (LB) method, ink-jet printing, laser-printing,and/or laser-induced thermal imaging. When the hole blocking layer isformed by vacuum deposition and/or spin coating, deposition and coatingconditions for the hole blocking layer may be determined by referring tothe deposition and coating conditions for the hole injection layer.

The hole blocking layer may include, for example, at least one selectedfrom BCP and Bphen, but is not limited thereto:

A thickness of the hole blocking layer may be in a range of about 20 Åto about 1,000 Å, for example, about 30 Å to about 300 Å. When thethickness of the hole blocking layer is within any of these ranges, thehole blocking layer may have excellent (or suitable) hole blockingcharacteristics without a substantial increase in driving voltage.

The electron transport region may be disposed between the emission layerand the second electrode, and may include an electron transport layerand at least one selected from a hole blocking layer and an electroninjection layer.

For example, the electron transport region may have a structure ofelectron transport layer/electron injection layer or a structure of holeblocking layer/electron transport layer/electron injection layer,wherein the layers of each structure are sequentially stacked from theemission layer in the stated order, but the structure of the electrontransport region is not limited thereto.

According to an embodiment, the organic layer 150 of the organiclight-emitting device includes an electron transport region disposedbetween the emission layer and the second electrode 190, and theelectron transport region may include an electron transport layer. Theelectron transport layer may include a plurality of layers. For example,the electron transport layer may include a first electron transportlayer and a second electron transport layer.

The electron transport layer may include the compound of Formula 1according to an embodiment of the present disclosure.

A thickness of the electron transport layer may be in a range of about100 Å to about 1,000 Å, for example, about 150 Å to about 500 Å. Whenthe thickness of the electron transport layer is within any of theranges described above, the electron transport layer may havesatisfactory (or suitable) electron transport characteristics without asubstantial increase in driving voltage.

The electron transport layer may further include, in addition to thematerials described above, a metal-containing material.

The metal-containing material may include a Li complex. The Li complexmay include, for example, Compound ET-D1 (lithium quinolate, LiQ) and/orCompound ET-D2.

In some embodiments, the electron transport region may include anelectron injection layer that facilitates injection of electrons fromthe second electrode 190.

The electron injection layer may be formed on the electron transportlayer by using one or more suitable methods such as vacuum deposition,spin coating, casting, a LB method, ink-jet printing, laser-printing,and/or laser-induced thermal imaging. When an electron injection layeris formed by vacuum deposition and/or spin coating, deposition andcoating conditions for the electron injection layer may be the same as(or substantially similar to) those for the hole injection layer.

The electron injection layer may include at least one selected from LiF,NaCl, CsF, Li₂O, BaO, and LiQ.

A thickness of the electron injection layer may be in a range of about 1Å to about 100 Å, for example, about 3 Å to about 90 Å. When thethickness of the electron injection layer is within any of the rangesdescribed above, the electron injection layer may have satisfactory (orsuitable) electron injection characteristics without a substantialincrease in driving voltage.

The second electrode 190 may be disposed on the organic layer 150 havingthe structure according to embodiments of the present disclosure. Thesecond electrode 190 may be a cathode, which is an electron injectionelectrode, and in this regard, a material for forming the secondelectrode 190 may be selected from a metal, an alloy, an electricallyconductive compound, and a mixture thereof, which have a relatively lowwork function. Non-limiting examples of the material for forming thesecond electrode 190 include lithium (Li), magnesium (Mg), aluminum(Al), aluminum-lithium (Al—Li), calcium (Ca), magnesium-indium (Mg—In),and magnesium-silver (Mg—Ag). In some embodiments, the material forforming the second electrode 190 may be ITO and/or IZO. The secondelectrode 190 may be a reflective electrode, a semi-transmissiveelectrode, or a transmissive electrode.

An organic layer according to an embodiment of the present disclosuremay be formed by depositing the compound according to an embodiment, ormay be formed by using a wet method in which the compound according toan embodiment is prepared in the form of a solution and then thesolution of the compound is used for coating.

An organic light-emitting device according to an embodiment may be usedin various flat panel display apparatuses, such as a passive matrixorganic light-emitting display apparatus and/or an active matrix organiclight-emitting display apparatus. For example, when the organiclight-emitting device is included in an active matrix organiclight-emitting display apparatus, a first electrode disposed on asubstrate may act as a pixel electrode and may be electrically connected(e.g., coupled) to a source electrode or a drain electrode of a thinfilm transistor. In addition, the organic light-emitting device may beincluded in a flat panel display apparatus that emits light in oppositedirections (e.g., emits light from both sides of a display panel).

Hereinbefore, the organic light-emitting device has been described withreference to the drawing, but embodiments of the present disclosure arenot limited thereto.

Hereinafter, definitions of substituents used herein will be presented.The number of carbon atoms used to restrict a substituent is notlimited, and does not limit properties of the substituent, and unlessdefined otherwise, the definition of the substituent is consistent witha general definition thereof.

A C₁-C₆₀ alkyl group used herein may refer to a linear or branchedaliphatic hydrocarbon monovalent group having 1 to 60 carbon atoms, andnon-limiting examples thereof are a methyl group, an ethyl group, apropyl group, an isobutyl group, a sec-butyl group, a tert-butyl group,a pentyl group, an iso-amyl group, and a hexyl group. A C₁-C₆₀ alkylenegroup used herein may refer to a divalent group having the samestructure as the C₁-C₆₀ alkyl group.

A C₁-C₆₀ alkoxy group used herein may refer to a monovalent grouprepresented by —OA₁₀₁ (wherein A₁₀₁ is the C₁-C₆₀ alkyl group), andnon-limiting examples thereof are a methoxy group, an ethoxy group, andan isopropoxy group.

A C₂-C₆₀ alkenyl group used herein may refer to a hydrocarbon grouphaving at least one carbon double bond at one or more positions alongthe hydrocarbon chain of the C₂-C₆₀ alkyl group (e.g., in the middle orat either terminal end of the C₂-C₆₀ alkyl group), and non-limitingexamples thereof are an ethenyl group, a propenyl group, and a butenylgroup. A C₂-C₆₀ alkenylene group used herein may refer to a divalentgroup having the same structure as the C₂-C₆₀ alkenyl group.

A C₂-C₆₀ alkynyl group used herein may refer to a hydrocarbon grouphaving at least one carbon triple bond at one or more positions alongthe hydrocarbon chain of the C₂-C₆₀ alkyl group (e.g., in the middle orat either terminal end of the C₂-C₆₀ alkyl group), and non-limitingexamples thereof are an ethynyl group and a propynyl group. A C₂-C₆₀alkynylene group used herein may refer to a divalent group having thesame structure as the C₂-C₆₀ alkynyl group.

A C₃-C₁₀ cycloalkyl group used herein may refer to a monovalenthydrocarbon monocyclic group having 3 to 10 carbon atoms, andnon-limiting examples thereof are a cyclopropyl group, a cyclobutylgroup, a cyclopentyl group, a cyclohexyl group, and a cycloheptyl group.A C₃-C₁₀ cycloalkylene group used herein may refer to a divalent grouphaving the same structure as the C₃-C₁₀ cycloalkyl group.

A C₂-C₁₀ heterocycloalkyl group used herein may refer to a monovalentmonocyclic group having at least one heteroatom selected from N, O, P,and S as a ring-forming atom, and 2 to 10 carbon atoms, and non-limitingexamples thereof are a tetrahydrofuranyl group and atetrahydrothiophenyl group. A C₂-C₁₀ heterocycloalkylene group usedherein may refer to a divalent group having the same structure as theC₂-C₁₀ heterocycloalkyl group.

A C₃-C₁₀ cycloalkenyl group used herein may refer to a monovalentmonocyclic group that has 3 to 10 carbon atoms and at least one doublebond in the ring thereof and does not have aromaticity, and non-limitingexamples thereof are a cyclopentenyl group, a cyclohexenyl group, and acycloheptenyl group. A C₃-C₁₀ cycloalkenylene group used herein mayrefer to a divalent group having the same structure as the C₃-C₁₀cycloalkenyl group.

A C₂-C₁₀ heterocycloalkenyl group used herein may refer to a monovalentmonocyclic group that has at least one heteroatom selected from N, O, P,and S as a ring-forming atom, 2 to 10 carbon atoms, and at least onedouble bond in its ring. Non-limiting examples of the C₂-C₁₀heterocycloalkenyl group are a 2,3-hydrofuranyl group and a2,3-hydrothiophenyl group. A C₂-C₁₀ heterocycloalkenylene group usedherein may refer to a divalent group having the same structure as theC₂-C₁₀ heterocycloalkenyl group.

A C₆-C₆₀ aryl group used herein may refer to a monovalent group having acarbocyclic aromatic system having 6 to 60 carbon atoms, and a C₆-C₆₀arylene group used herein may refer to a divalent group having acarbocyclic aromatic system having 6 to 60 carbon atoms. Non-limitingexamples of the C₆-C₆₀ aryl group are a phenyl group, a biphenyl group,a terphenyl group, a naphthyl group, an anthracenyl group, aphenanthrenyl group, a pyrenyl group, and a chrysenyl group. When theC₆-C₆₀ aryl group and the C₆-C₆₀ arylene group each independentlyinclude two or more rings, the respective rings may be fused to eachother.

A C₁-C₆₀ heteroaryl group used herein may refer to a monovalent grouphaving a carbocyclic aromatic system that has at least one heteroatomselected from N, O, P, and S as a ring-forming atom, and 1 to 60 carbonatoms. A C₁-C₆₀ heteroarylene group used herein may refer to a divalentgroup having a carbocyclic aromatic system that has at least oneheteroatom selected from N, O, P, and S as a ring-forming atom, and 1 to60 carbon atoms. Non-limiting examples of the C₁-C₆₀ heteroaryl groupare a pyridinyl group, a pyrimidinyl group, a pyrazinyl group, apyridazinyl group, a triazinyl group, a quinolinyl group, and anisoquinolinyl group. When the C₁-C₆₀ heteroaryl group and the C₁-C₆₀heteroarylene group each independently include two or more rings, therespective rings may be fused to each other.

A C₆-C₆₀ aryloxy group used herein may refer to a monovalent grouprepresented by —OA₁₀₂ (where A₁₀₂ is the C₆-C₆₀ aryl group), and aC₆-C₆₀ arylthio group may refer to a monovalent group represented by—SA₁₀₃ (where A₁₀₃ is the C₆-C₆₀ aryl group).

A monovalent non-aromatic condensed polycyclic group used herein mayrefer to a monovalent group that has two or more rings condensed (e.g.,fused) to each other, only carbon atoms as ring forming atoms (e.g., 8to 60 carbon atoms), and non-aromaticity in the entire molecularstructure (e.g., does not have overall aromaticity). A non-limitingexample of the monovalent non-aromatic condensed polycyclic group is afluorenyl group. A divalent non-aromatic condensed polycyclic group usedherein may refer to a divalent group having the same structure as themonovalent non-aromatic condensed polycyclic group.

A monovalent non-aromatic condensed heteropolycyclic group used hereinmay refer to a monovalent group that has two or more rings condensed(e.g., fused) to each other, has at least one heteroatom selected fromN, O, P, and S, other than carbon atoms (e.g., 2 to 60 carbon atoms), asring forming atoms, and has non-aromaticity in the entire molecularstructure (e.g., does not have overall aromaticity). A divalentnon-aromatic condensed heteropolycyclic group used herein may refer to adivalent group having the same structure as the monovalent non-aromaticcondensed heteropolycyclic group.

As used herein, at least one substituent of the substituted C₃-C₁₀cycloalkylene group, substituted C₂-C₁₀ heterocycloalkylene group,substituted C₃-C₁ cycloalkenylene group, substituted C₂-C₁₀heterocycloalkenylene group, substituted C₆-C₆₀ arylene group,substituted C₁-C₆₀ heteroarylene group, a substituted divalentnon-aromatic condensed polycyclic group, a substituted divalentnon-aromatic condensed heteropolycyclic group, substituted C₁-C₆₀ alkylgroup, substituted C₂-C₆₀ alkenyl group, substituted C₂-C₆₀ alkynylgroup, substituted C₁-C₆₀ alkoxy group, substituted C₃-C₁₀ cycloalkylgroup, substituted C₂-C₁₀ heterocycloalkyl group, substituted C₃-C₁₀cycloalkenyl group, substituted C₂-C₁₀ heterocycloalkenyl group,substituted C₆-C₆₀ aryl group, substituted C₆-C₆₀ aryloxy group,substituted C₆-C₆₀ arylthio group, substituted C₁-C₆₀ heteroaryl group,substituted monovalent non-aromatic condensed polycyclic group, andsubstituted monovalent non-aromatic condensed heteropolycyclic group maybe selected from the group consisting of:

deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitrogroup, an amino group, an amidino group, a hydrazine group, a hydrazonegroup, a carboxylic acid group or a salt thereof, a sulfonic acid groupor a salt thereof, a phosphoric acid group or a salt thereof, a C₁-C₆₀alkyl group, a C₂-C₆₀ alkenyl group, a C₂-C₆₀ alkynyl group, and aC₁-C₆₀ alkoxy group,

a C₁-C₆₀ alkyl group, a C₂-C₆₀ alkenyl group, a C₂-C₆₀ alkynyl group,and a C₁-C₆₀ alkoxy group, each substituted with at least one selectedfrom deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, anitro group, an amino group, an amidino group, a hydrazine group, ahydrazone group, a carboxylic acid group or a salt thereof, a sulfonicacid group or a salt thereof, a phosphoric acid group or a salt thereof,a C₃-C₁₀ cycloalkyl group, a C₂-C₁₀ heterocycloalkyl group, a C₃-C₁₀cycloalkenyl group, a C₂-C₁₀ heterocycloalkenyl group, a C₆-C₆₀ arylgroup, a C₆-C₆₀ aryloxy group, a C₆-C₆₀ arylthio group, a C₁-C₆₀heteroaryl group, a monovalent non-aromatic condensed polycyclic group,a monovalent non-aromatic condensed heteropolycyclic group,—N(Q₁₁)(Q₁₂), —Si(Q₁₃)(Q₁₄)(Q₁₅), and —B(Q₁₆)(Q₁₇),

a C₃-C₁₀ cycloalkyl group, a C₂-C₁₀ heterocycloalkyl group, a C₃-C₁₀cycloalkenyl group, a C₂-C₁₀ heterocycloalkenyl group, a C₆-C₆₀ arylgroup, a C₆-C₆₀ aryloxy group, a C₆-C₆₀ arylthio group, a C₁-C₆₀heteroaryl group, a monovalent non-aromatic condensed polycyclic group,and a monovalent non-aromatic condensed heteropolycyclic group,

a C₃-C₁₀ cycloalkyl group, a C₂-C₁₀ heterocycloalkyl group, a C₃-C₁₀cycloalkenyl group, a C₂-C₁₀ heterocycloalkenyl group, a C₆-C₆₀ arylgroup, a C₆-C₆₀ aryloxy group, a C₆-C₆₀ arylthio group, a C₁-C₆₀heteroaryl group, a monovalent non-aromatic condensed polycyclic group,and a monovalent non-aromatic condensed heteropolycyclic group, eachsubstituted with at least one selected from deuterium, —F, —Cl, —Br, —I,a hydroxyl group, a cyano group, a nitro group, an amino group, anamidino group, a hydrazine group, a hydrazone group, a carboxylic acidgroup or a salt thereof, a sulfonic acid group or a salt thereof, aphosphoric acid group or a salt thereof, a C₁-C₆₀ alkyl group, a C₂-C₆₀alkenyl group, a C₂-C₆₀ alkynyl group, a C₁-C₆₀ alkoxy group, a C₃-C₁₀cycloalkyl group, a C₂-C₁₀ heterocycloalkyl group, a C₃-C₁₀ cycloalkenylgroup, a C₂-C₁₀ heterocycloalkenyl group, a C₆-C₆₀ aryl group, a C₆-C₆₀aryloxy group, a C₆-C₆₀ arylthio group, a C₁-C₆₀ heteroaryl group, amonovalent non-aromatic condensed polycyclic group, a monovalentnon-aromatic condensed heteropolycyclic group, —N(Q₂₁)(Q₂₂),—Si(Q₂₃)(Q₂₄)(Q₂₅) and —B(Q₂₆)(Q₂₇), and

—N(Q₃₁)(Q₃₂), —Si(Q₃₃)(Q₃₄)(Q₃₅) and —B(Q₃₆)(Q₃₇),

wherein Q₁₁ to Q₁₇, Q₂₁ to Q₂₇ and Q₃₁ to Q₃₇ may each independently beselected from hydrogen, deuterium, —F, —Cl, —Br, —I, a hydroxyl group, acyano group, a nitro group, an amino group, an amidino group, ahydrazine group, a hydrazone group, a carboxylic acid group or a saltthereof, a sulfonic acid group or a salt thereof, a phosphoric acidgroup or a salt thereof, a C₁-C₆₀ alkyl group, a C₂-C₆₀ alkenyl group, aC₂-C₆₀ alkynyl group, a C₁-C₆₀ alkoxy group, a C₃-C₁₀ cycloalkyl group,a C₂-C₁ heterocycloalkyl group, a C₃-C₁₀ cycloalkenyl group, a C₂-C₁₀heterocycloalkenyl group, a C₆-C₆₀ aryl group, a C₁-C₆₀ heteroarylgroup, a monovalent non-aromatic condensed polycyclic group, and amonovalent non-aromatic condensed heteropolycyclic group.

For example, at least one substituent of the substituted C₃-C₁₀cycloalkylene group, substituted C₂-C₁₀ heterocycloalkylene group,substituted C₃-C₁₀ cycloalkenylene group, substituted C₂-C₁₀heterocycloalkenylene group, substituted C₆-C₆₀ arylene group,substituted C₁-C₆₀ heteroarylene group, a substituted divalentnon-aromatic condensed polycyclic group, a substituted divalentnon-aromatic condensed heteropolycyclic group, substituted C₁-C₆₀ alkylgroup, substituted C₂-C₆₀ alkenyl group, substituted C₂-C₆₀ alkynylgroup, substituted C₁-C₆₀ alkoxy group, substituted C₃-C₁₀ cycloalkylgroup, substituted C₂-C₁₀ heterocycloalkyl group, substituted C₃-C₁₀cycloalkenyl group, substituted C₂-C₁₀ heterocycloalkenyl group,substituted C₆-C₆₀ aryl group, substituted C₆-C₆₀ aryloxy group,substituted C₆-C₆₀ arylthio group, substituted C₁-C₆₀ heteroaryl group,substituted monovalent non-aromatic condensed polycyclic group, andsubstituted monovalent non-aromatic condensed heteropolycyclic group maybe selected from the group consisting of:

deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitrogroup, an amino group, an amidino group, a hydrazine group, a hydrazonegroup, a carboxylic acid group or a salt thereof, a sulfonic acid groupor a salt thereof, a phosphoric acid group or a salt thereof, a C₁-C₆₀alkyl group, a C₂-C₆₀ alkenyl group, a C₂-C₆₀ alkynyl group, and aC₁-C₆₀ alkoxy group,

a C₁-C₆₀ alkyl group, a C₂-C₆₀ alkenyl group, a C₂-C₆₀ alkynyl group,and a C₁-C₆₀ alkoxy group, each substituted with at least one selectedfrom deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, anitro group, an amino group, an amidino group, a hydrazine group, ahydrazone group, a carboxylic acid group or a salt thereof, a sulfonicacid group or a salt thereof, a phosphoric acid group or a salt thereof,a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, acyclopentenyl group, a cyclohexenyl group, a phenyl group, a pentalenylgroup, an indenyl group, a naphthyl group, an azulenyl group, aheptalenyl group, an indacenyl group, an acenaphthyl group, a fluorenylgroup, a spiro-fluorenyl group, a benzofluorenyl group, adibenzofluorenyl group, a phenalenyl group, a phenanthrenyl group, ananthracenyl group, a fluoranthenyl group, a triphenylenyl group, apyrenyl group, a chrysenyl group, a naphthacenyl group, a picenyl group,a perylenyl group, a pentaphenyl group, a hexacenyl group, a pentacenylgroup, a rubicenyl group, a coronenyl group, an ovalenyl group, apyrrolyl group, a thiophenyl group, a furanyl group, an imidazolylgroup, a pyrazolyl group, a thiazolyl group, an isothiazolyl group, anoxazolyl group, an isoxazolyl group, a pyridinyl group, a pyrazinylgroup, a pyrimidinyl group, a pyridazinyl group, an isoindolyl group, anindolyl group, an indazolyl group, a purinyl group, a quinolinyl group,an isoquinolinyl group, a benzoquinolinyl group, a phthalazinyl group, anaphthyridinyl group, a quinoxalinyl group, a quinazolinyl group, acinnolinyl group, a carbazolyl group, a phenanthridinyl group, anacridinyl group, a phenanthrolinyl group, a phenazinyl group, abenzoimidazolyl group, a benzofuranyl group, a benzothiophenyl group, anisobenzothiazolyl group, a benzoxazolyl group, an isobenzoxazolyl group,a triazolyl group, a tetrazolyl group, an oxadiazolyl group, a triazinylgroup, a dibenzofuranyl group, a dibenzothiophenyl group, abenzocarbazolyl group, a dibenzocarbazolyl group, a thiadiazolyl group,an imidazopyridinyl group, an imidazopyrimidinyl group, —N(Q₁₁)(Q₁₂),—Si(Q₁₃)(Q₁₄)(Q₁₅), and —B(Q₁₆)(Q₁₇),

a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, acyclopentenyl group, a cyclohexenyl group, a phenyl group, a pentalenylgroup, an indenyl group, a naphthyl group, an azulenyl group, aheptalenyl group, an indacenyl group, an acenaphthyl group, a fluorenylgroup, a spiro-fluorenyl group, a benzofluorenyl group, adibenzofluorenyl group, a phenalenyl group, a phenanthrenyl group, ananthracenyl group, a fluoranthenyl group, a triphenylenyl group, apyrenyl group, a chrysenyl group, a naphthacenyl group, a picenyl group,a perylenyl group, a pentaphenyl group, a hexacenyl group, a pentacenylgroup, a rubicenyl group, a coronenyl group, an ovalenyl group, apyrrolyl group, a thiophenyl group, a furanyl group, an imidazolylgroup, a pyrazolyl group, a thiazolyl group, an isothiazolyl group, anoxazolyl group, an isoxazolyl group, a pyridinyl group, a pyrazinylgroup, a pyrimidinyl group, a pyridazinyl group, an isoindolyl group, anindolyl group, an indazolyl group, a purinyl group, a quinolinyl group,an isoquinolinyl group, a benzoquinolinyl group, a phthalazinyl group, anaphthyridinyl group, a quinoxalinyl group, a quinazolinyl group, acinnolinyl group, a carbazolyl group, a phenanthridinyl group, anacridinyl group, a phenanthrolinyl group, a phenazinyl group, abenzoimidazolyl group, a benzofuranyl group, a benzothiophenyl group, anisobenzothiazolyl group, a benzoxazolyl group, an isobenzoxazolyl group,a triazolyl group, a tetrazolyl group, an oxadiazolyl group, a triazinylgroup, a dibenzofuranyl group, a dibenzothiophenyl group, abenzocarbazolyl group, a dibenzocarbazolyl group, a thiadiazolyl group,an imidazopyridinyl group, and an imidazopyrimidinyl group,

a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, acyclopentenyl group, a cyclohexenyl group, a phenyl group, a pentalenylgroup, an indenyl group, a naphthyl group, an azulenyl group, aheptalenyl group, an indacenyl group, an acenaphthyl group, a fluorenylgroup, a spiro-fluorenyl group, a benzofluorenyl group, adibenzofluorenyl group, a phenalenyl group, a phenanthrenyl group, ananthracenyl group, a fluoranthenyl group, a triphenylenyl group, apyrenyl group, a chrysenyl group, a naphthacenyl group, a picenyl group,a perylenyl group, a pentaphenyl group, a hexacenyl group, a pentacenylgroup, a rubicenyl group, a coronenyl group, an ovalenyl group, apyrrolyl group, a thiophenyl group, a furanyl group, an imidazolylgroup, a pyrazolyl group, a thiazolyl group, an isothiazolyl group, anoxazolyl group, an isoxazolyl group, a pyridinyl group, a pyrazinylgroup, a pyrimidinyl group, a pyridazinyl group, an isoindolyl group, anindolyl group, an indazolyl group, a purinyl group, a quinolinyl group,an isoquinolinyl group, a benzoquinolinyl group, a phthalazinyl group, anaphthyridinyl group, a quinoxalinyl group, a quinazolinyl group, acinnolinyl group, a carbazolyl group, a phenanthridinyl group, anacridinyl group, a phenanthrolinyl group, a phenazinyl group, abenzoimidazolyl group, a benzofuranyl group, a benzothiophenyl group, anisobenzothiazolyl group, a benzoxazolyl group, an isobenzoxazolyl group,a triazolyl group, a tetrazolyl group, an oxadiazolyl group, a triazinylgroup, a dibenzofuranyl group, a dibenzothiophenyl group, abenzocarbazolyl group, a dibenzocarbazolyl group, a thiadiazolyl group,an imidazopyridinyl group, and an imidazopyrimidinyl group, eachsubstituted with at least one selected from deuterium, —F, —Cl, —Br, —I,a hydroxyl group, a cyano group, a nitro group, an amino group, anamidino group, a hydrazine group, a hydrazone group, a carboxylic acidgroup or a salt thereof, a sulfonic acid group or a salt thereof, aphosphoric acid group or a salt thereof, a C₁-C₆₀ alkyl group, a C₂-C₆₀alkenyl group, a C₂-C₆₀ alkynyl group, a C₁-C₆₀ alkoxy group, acyclopentyl group, a cyclohexyl group, a cycloheptyl group, acyclopentenyl group, a cyclohexenyl group, a phenyl group, a pentalenylgroup, an indenyl group, a naphthyl group, an azulenyl group, aheptalenyl group, an indacenyl group, an acenaphthyl group, a fluorenylgroup, a spiro-fluorenyl group, a benzofluorenyl group, adibenzofluorenyl group, a phenalenyl group, a phenanthrenyl group, ananthracenyl group, a fluoranthenyl group, a triphenylenyl group, apyrenyl group, a chrysenyl group, a naphthacenyl group, a picenyl group,a perylenyl group, a pentaphenyl group, a hexacenyl group, a pentacenylgroup, a rubicenyl group, a coronenyl group, an ovalenyl group, apyrrolyl group, a thiophenyl group, a furanyl group, an imidazolylgroup, a pyrazolyl group, a thiazolyl group, an isothiazolyl group, anoxazolyl group, an isoxazolyl group, a pyridinyl group, a pyrazinylgroup, a pyrimidinyl group, a pyridazinyl group, an isoindolyl group, anindolyl group, an indazolyl group, a purinyl group, a quinolinyl group,an isoquinolinyl group, a benzoquinolinyl group, a phthalazinyl group, anaphthyridinyl group, a quinoxalinyl group, a quinazolinyl group, acinnolinyl group, a carbazolyl group, a phenanthridinyl group, anacridinyl group, a phenanthrolinyl group, a phenazinyl group, abenzoimidazolyl group, a benzofuranyl group, a benzothiophenyl group, anisobenzothiazolyl group, a benzoxazolyl group, an isobenzoxazolyl group,a triazolyl group, a tetrazolyl group, an oxadiazolyl group, a triazinylgroup, a dibenzofuranyl group, a dibenzothiophenyl group, abenzocarbazolyl group, a dibenzocarbazolyl group, a thiadiazolyl group,an imidazopyridinyl group, an imidazopyrimidinyl group, —N(Q₂₁)(Q₂₂),—Si(Q₂₃)(Q₂₄)(Q₂₅), and —B(Q₂₆)(Q₂₇), and

—N(Q₃₁)(Q₃₂), —Si(Q₃₃)(Q₃₄)(Q₃₅), and —B(Q₃₆)(Q₃₇),

wherein Q₁₁ to Q₁₇, Q₂₁ to Q₂₇, and Q₃₁ to Q₃₇ may each independently beselected from hydrogen, deuterium, —F, —Cl, —Br, —I, a hydroxyl group, acyano group, a nitro group, an amino group, an amidino group, ahydrazine group, a hydrazone group, a carboxylic acid group or a saltthereof, a sulfonic acid group or a salt thereof, a phosphoric acidgroup or a salt thereof, a C₁-C₆₀ alkyl group, a C₂-C₆₀ alkenyl group, aC₂-C₆₀ alkynyl group, a C₁-C₆₀ alkoxy group, a cyclopentyl group, acyclohexyl group, a cycloheptyl group, a cyclopentenyl group, acyclohexenyl group, a phenyl group, a pentalenyl group, an indenylgroup, a naphthyl group, an azulenyl group, a heptalenyl group, anindacenyl group, an acenaphthyl group, a fluorenyl group, aspiro-fluorenyl group, a benzofluorenyl group, a dibenzofluorenyl group,a phenalenyl group, a phenanthrenyl group, an anthracenyl group, afluoranthenyl group, a triphenylenyl group, a pyrenyl group, a chrysenylgroup, a naphthacenyl group, a picenyl group, a perylenyl group, apentaphenyl group, a hexacenyl group, a pentacenyl group, a rubicenylgroup, a coronenyl group, an ovalenyl group, a pyrrolyl group, athiophenyl group, a furanyl group, an imidazolyl group, a pyrazolylgroup, a thiazolyl group, an isothiazolyl group, an oxazolyl group, anisoxazolyl group, a pyridinyl group, a pyrazinyl group, a pyrimidinylgroup, a pyridazinyl group, an isoindolyl group, an indolyl group, anindazolyl group, a purinyl group, a quinolinyl group, an isoquinolinylgroup, a benzoquinolinyl group, a phthalazinyl group, a naphthyridinylgroup, a quinoxalinyl group, a quinazolinyl group, a cinnolinyl group, acarbazolyl group, a phenanthridinyl group, an acridinyl group, aphenanthrolinyl group, a phenazinyl group, a benzoimidazolyl group, abenzofuranyl group, a benzothiophenyl group, an isobenzothiazolyl group,a benzoxazolyl group, an isobenzoxazolyl group, a triazolyl group, atetrazolyl group, an oxadiazolyl group, a triazinyl group, adibenzofuranyl group, a dibenzothiophenyl group, a benzocarbazolylgroup, a dibenzocarbazolyl group, a thiadiazolyl group, animidazopyridinyl group, and an imidazopyrimidinyl group.

The expression “Ph” used herein may refer to a phenyl group, theexpression “Me” used herein may refer to a methyl group, the expression“Et” used herein may refer to an ethyl group, the expression “ter-Bu” or“Bu^(t)” used herein may refer to a tert-butyl group, and “D” may referto deuterium.

Hereinafter, an organic light-emitting device according to one or moreembodiments of the present disclosure will be described in more detailwith reference to Synthesis Examples and Examples.

SYNTHESIS EXAMPLE Synthesis Example 1: Synthesis of Compound 2

Synthesis of Intermediate I-1

2.58 g (10 mmol) of 10-bromobenzo[h]quinoline was dissolved in 40 mL oftetrahydrofuran (THF), and then 4 mL of n-butyllithium (n-BuLi) (2.5molar (M) in hexane) was added thereto at −78° C. 1 hour after theaddition, at the same temperature, 2.0 mL (10 mmol) of2-isopropoxy-4,4,5,5-tetramethyl-1,3,2-dioxaborolane was added thereto.The result was stirred at ambient temperature for 10 hours, water wasadded thereto, and the result washed three times with 30 mL of diethylether. The washed diethyl ether layer was dried by using magnesiumsulfate (MgSO₄) and then dried under reduced pressure to obtain aproduct, which was then separation-purified by silica gel columnchromatography, thereby completing the preparation of 1.86 g ofIntermediate I-1 (yield: 61%). The obtained compound was identified byliquid chromatography-mass spectrometry (LC-MS). C₁₉H₂₀BNO₂: M+1 306.2.

Synthesis of Intermediate I-2

3.05 g (10.0 mmol) of Intermediate I-1, 2.02 g (10.0 mmol) of1-bromo-2-nitrobenzene, 0.58 g (0.50 mmol) of Pd(PPh₃)₄, 0.16 g (0.5mmol) of tetrabutylammonium bromide (TBAB), and 3.18 g (30.0 mmol) ofNa₂CO₃ were dissolved in 60 mL of a toluene/ethanol/H₂O (3/3/1) mixedsolution, and then, the resulting mixture was stirred at a temperatureof 80° C. for 16 hours. The obtained reaction solution was cooled toambient temperature, and then, an extraction process was performedthereon three times by using 60 mL of water and 60 mL of diethyl ether.An organic layer obtained therefrom was dried by using MgSO₄ and theresidual obtained by evaporating a solvent therefrom wasseparation-purified by silica gel column chromatography, therebycompleting the preparation of 2.34 g of Intermediate I-2 (yield: 78%).The obtained compound was identified by LC-MS. C₁₉H₁₂N₂O₂: M+1 301.1.

Synthesis of Intermediate I-3

3.00 g (10.0 mmol) of Intermediate I-2, 3.56 g (30 mmol) of tin, and 5mL (50 mmol, conc. 36.5%) of hydrochloric acid were dissolved in 60 mLof ethanol, and then the mixture was stirred at a temperature of 100° C.for 8 hours. The reaction solution was cooled to ambient temperature,and 3 g of sodium hydroxide dissolved in 10 mL of water was added to afiltrate obtained by performing filtration of the reaction solutionunder reduced pressure, and an extraction process was performed thereonthree times by using 60 mL of water and 60 mL of dichloromethane. Anorganic layer obtained therefrom was dried by using MgSO₄ and theresidual obtained by evaporating a solvent therefrom wasseparation-purified by silica gel column chromatography, therebycompleting the preparation of 2.51 g of Intermediate I-3 (yield: 93%).The obtained compound was identified by LC-MS. C₁₉H₁₄N₂: M+1 271.1.

Synthesis of Intermediate I-4

2.70 g (10 mmol) of Intermediate I-3 was dissolved in 30 mL of THF, 4 mLof triethanolamine (TEA) and 3.29 g (15 mmol) of 4-bromobenzoyl chloridewere slowly added thereto at a temperature of 0° C., and then theresulting mixture was stirred at ambient temperature for about 10 hours.Once the reaction was complete, an extraction process was performedthereon three times by using 40 mL of water and 40 mL of ethylacetate.An organic layer obtained therefrom was dried by using MgSO₄ and theresidual obtained by evaporating a solvent therefrom wasseparation-purified by silica gel column chromatography, therebycompleting the preparation of 3.62 g of Intermediate I-4 (yield: 80%).The obtained compound was identified by LC-MS. C₂₆H₁₇BrN₂O: M+1 453.1.

Synthesis of Intermediate I-5

4.53 g (10 mmol) of Intermediate I-4 and P₂O₅ were dissolved in 60 mL ofPOCl₃, and then the resulting mixture was stirred at a temperature of105° C. for 24 hours. Once the reaction was complete, the solvent wasremoved therefrom, neutralized using NaOH, and an extraction process wasperformed thereon by using ethyl acetate. An organic layer obtainedtherefrom was dried by using MgSO₄ and the residual obtained byevaporating a solvent therefrom was separation-purified by silica gelcolumn chromatography, thereby completing the preparation of 2.61 g ofIntermediate I-5 (yield: 66%). The obtained compound was identified byLC-MS. C₂₆H₁₅BrN₂: M+1 435.0.

Synthesis of Intermediate I-6

3.57 g of Intermediate I-6 (yield: 74%) was obtained in the same (orsubstantially the same) manner as in Synthesis of Intermediate I-1,except that Intermediate I-5 was used instead of10-bromobenzo[h]quinoline. The obtained compound was identified byLC-MS. C₃₂H₂₇BN₂O₂: M+1 483.2.

Synthesis of Compound 2

4.82 g (10 mmol) of Intermediate I-6, 2.68 g (10 mmol) of2-chloro-4,6-diphenyl-1,3,5-triazine, 0.58 g (0.5 mmol) oftetrakis(triphenylphosphine)palladium (Pd(PPh₃)₃), and 4.14 g (30 mmol)of K₂CO₃ were dissolved in 60 mL of a mixture solution of THF and H₂O(at a volume ratio of 2:1), and stirred at 80° C. for 16 hours. Theresulting solution was allowed to come to ambient temperature. Then, anextraction process was performed thereon three times by using each of 40mL of water and 50 mL of ethyl ether. The obtained organic layer wasdried by using MgSO₄. A solvent was next removed therefrom byevaporation. The residual was separation-purified through silica gelcolumn chromatography, thereby completing the preparation of 4.41 g ofCompound 2 (yield: 75%). The obtained compound was identified by massspectroscopy/fast atom bombardment (MS/FAB) and ¹H nuclear magneticresonance (NMR). Cc H₂₅N₅ cal. 587.21. found 587.20.

Synthesis Example 2: Synthesis of Compound 15

4.35 g (10 mmol) of Intermediate I-5 was dissolved in 60 mL of THF, andthen 4 mL of n-BuLi (2.5 M in hexane) was added thereto at −78° C. Onehour after the addition of n-BuLi, 2.20 g (10 mmol) of chlorodiphenylphosphine was slowly added dropwise thereto, and then the result wasstirred for about 3 hours and heated up to ambient temperature. Waterwas added thereto and the result was washed with 30 mL of ethyl acetatethree times. The washed ethyl acetate layer was dried by using MgSO₄ andthen dried under reduced pressure to obtain Intermediate I-7.Intermediate I-7 was dissolved in 40 mL of dichloromethane, 4 mL ofhydrogen peroxide was added thereto, and the resulting solution wasstirred at ambient temperature for about 20 hours. 20 mL of water wasthen added thereto, and an extraction process was performed three timesthereon using 20 mL of dichloromethane. The obtained organic layer wasdried by using MgSO₄. A solvent was next removed therefrom byevaporation. The residual was separation-purified through silica gelcolumn chromatography, thereby completing the preparation of 3.89 g ofCompound 15 (yield: 70%). The obtained compound was identified by MS/FABand ¹H NMR. C₃₈H₂₅N₂OP cal. 556.17. found 556.18.

Synthesis Example 3: Synthesis of Compound 33

Synthesis of Intermediate I-8

3.40 g of Intermediate I-8 (yield: 75%) was obtained in the same (orsubstantially the same) manner as in Synthesis of Intermediate I-4,except that 3-bromobenzoyl chloride was used instead of 4-bromobenzoylchloride. The obtained compound was identified by LC-MS. C₂₆H₁₇BrN₂O:M+1 453.1.

Synthesis of Intermediate I-9

3.00 g of Intermediate I-9 (yield: 69%) was obtained in the same (orsubstantially the same) manner as in Synthesis of Intermediate I-5,except that Intermediate I-8 was used instead of Intermediate I-4. Theobtained compound was identified by LC-MS. C₂₆H₁₅BrN₂: M+1 435.0.

Synthesis of Compound 33

4.48 g of Compound 33 (yield: 72%) was obtained in the same (orsubstantially the same) manner as in Synthesis of Compound 2, exceptthat Intermediate I-9 was used instead of Intermediate I-6, andIntermediate A-1 was used instead of2-chloro-4,6-diphenyl-1,3,5-triazine. The obtained compound wasidentified by MS/FAB and ¹H NMR. C₄₅H₂₆N₄ cal. 622.22. found 622.23.

Synthesis Example 4: Synthesis of Compound 52

Synthesis of Intermediate I-10

3.52 g of Intermediate I-10 (yield: 70%) was obtained in the same (orsubstantially the same) manner as in Synthesis of Intermediate I-4,except that Intermediate A-2 was used instead of 4-bromobenzoylchloride. The obtained compound was identified by LC-MS. C₃₀H₁₉BrN₂O:M+1 503.1.

Synthesis of Intermediate I-11

3.54 g of Intermediate I-11 (yield: 73%) was obtained in the same (orsubstantially the same) manner as in Synthesis of Intermediate I-5,except that Intermediate I-10 was used instead of Intermediate I-4. Theobtained compound was identified by LC-MS. C₃₀H₁₇BrN₂: M+1 485.1.

Synthesis of Compound 52

3.85 g of Compound 52 (yield: 76%) was obtained in the same (orsubstantially the same) manner as in Synthesis of Compound 2, exceptthat Intermediate I-11 was used instead of Intermediate I-6, and4-cyanophenylboronic acid was used instead of2-chloro-4,6-diphenyl-1,3,5-triazine. The obtained compound wasidentified by MS/FAB and ¹H NMR. C₃₇H₂₁N₃ cal. 507.17. found 507.18.

Synthesis Example 5: Synthesis of Compound 84

Synthesis of Intermediate I-12

2.58 g of Intermediate I-12 (yield: 68%) was obtained in the same (orsubstantially the same) manner as in Synthesis of Intermediate I-2,except that 1,4-dibromo-2-nitrobenzene was used instead of1-bromo-2-nitrobenzene. The obtained compound was identified by LC-MS.C₁₉H₁₁BrN₂O₂: M+1 379.0.

Synthesis of Intermediate I-13

3.32 g of Intermediate I-13 (yield: 95%) was obtained in the same (orsubstantially the same) manner as in Synthesis of Intermediate I-3,except that Intermediate I-12 was used instead of Intermediate I-2. Theobtained compound was identified by LC-MS. C₁₉H₁₃BrN: M+1 349.0.

Synthesis of Intermediate I-14

3.44 g of Intermediate I-14 (yield: 76%) was obtained in the same (orsubstantially the same) manner as in Synthesis of Intermediate I-4,except that Intermediate I-13 was used instead of Intermediate I-3, andbenzaldehyde was used instead of 4-bromobenzoyl chloride. The obtainedcompound was identified by LC-MS. C₂₆H₁₇BrN₂O: M+1 453.1.

Synthesis of Intermediate I-15

2.91 g of Intermediate I-15 (yield: 67%) was obtained in the same (orsubstantially the same) manner as in Synthesis of Intermediate I-5,except that Intermediate I-14 was used instead of Intermediate I-4. Theobtained compound was identified by LC-MS. C₂₆H₁₅BrN₂: M+1 435.0.

Synthesis of Compound 84

4.06 g of Compound 84 (yield: 76%) was obtained in the same (orsubstantially the same) manner as in Synthesis of Compound 15, exceptthat Intermediate I-15 was used instead of Intermediate I-5. Theobtained compound was identified by MS/FAB and ¹H NMR. C₃₈H₂₅N₂OP cal.556.17. found 556.18.

Synthesis Example 6: Synthesis of Compound 106

Synthesis of Intermediate I-16

3.42 g of Intermediate I-16 (yield: 71%) was obtained in the same (orsubstantially the same) manner as in Synthesis of Intermediate I-1,except that Intermediate I-15 was used instead of10-bromobenzo[h]quinoline. The obtained compound was identified byLC-MS. C₃₂H₂₇BN₂O₂: M+1 483.2.

Synthesis of Compound 106

4.97 g of Compound 106 (yield: 70%) was obtained in the same (orsubstantially the same) manner as in Synthesis of Compound 2, exceptthat Intermediate I-16 was used instead of Intermediate I-6, andIntermediate I-9 was used instead of2-chloro-4,6-diphenyl-1,3,5-triazine. The obtained compound wasidentified by MS/FAB and ¹H NMR. C₅₂H₃₀N₄ cal. 710.25. found 710.24.

Synthesis Example 7: Synthesis of Compound 125

3.80 g of Compound 125 (yield: 60%) was obtained in the same (orsubstantially the same) manner as in Synthesis of Compound 2, exceptthat Intermediate I-16 was used instead of Intermediate I-6, andIntermediate A-3 was used instead of2-chloro-4,6-diphenyl-1,3,5-triazine. The obtained compound wasidentified by MS/FAB and ¹H NMR. C₄₇H₂₇N₃ cal. 633.22. found 633.21.

Methods of synthesizing compounds other than compounds shown in Table 1should be apparent to those skilled in the art by referring to thesynthesis pathways and raw materials described above.

TABLE 1 MS/FAB Compound ¹H NMR (CDCl₃ , 400 MHz) found calc. 2 δ =8.84-8.82 (dd, 1H), 8.73-8.70 (m, 4H), 8.63-8.60 (m, 587.20 587.21 2H),8.49-8.45 (m, 3H), 8.36-8.34 (m, 1H), 8.30-8.28 (m, 1H), 8.23-8.21 (m,1H), 7.92-7.88 (m, 2H), 7.76-7.72 (m, 2H), 7.63-7.53 (m, 5H), 7.49-7.46(m, 1H), 7.42-7.38 (m, 2H) 10 δ = 8.81-8.80 (dd, 1H), 8.49-8.47 (m, 1H),8.38-8.36 (m, 573.21 573.22 1H), 8.31-8.23 (m, 4H), 7.89-7.72 (m, 7H),7.67-7.65 (m, 1H), 7.57-7.42 (m, 6H), 1.59 (s, 6H) 15 δ = 8.78-8.76 (dd,1H), 8.49-8.47 (m, 1H), 8.37-8.35 (m, 556.18 556.17 1H), 8.31-8.29 (m,1H), 8.25-8.23 (m, 1H), 8.04-8.00 (m, 2H), 7.89-7.82 (m, 2H), 7.79-7.74(m, 3H), 7.70-7.65 (m, 5H), 7.57-7.40 (m, 8H) 18 δ = 9.66 (s, 1H),□8.78-8.64 (m, 5H), 8.60-8.56 (m, 3H), 587.20 587.21 8.51-8.49 (m, 3H),8.36-8.34 (m, 1H), 8.30-8.28 (m, 1H), 8.16-8.14 (m, 1H), 7.90-7.86 (m,1H), 7.74-7.70 (m, 1H), 7.65-7.53 (m, 6H), 7.42-7.38 (m, 2H) 27 δ = 9.67(s, 1H), 8.72-8.70 (m, 1H), 8.61-8.59 (m, 1H), 522.19 522.17 8.52-8.50(m, 1H), 8.37-8.35 (m, 1H), 8.32-8.30 (m, 1H), 8.22-8.15 (m, 3H),7.95-7.86 (m, 5H), 7.74-7.72 (m, 2H), 7.66-7.61 (m, 2H), 7.57-7.48 (m,2H), 7.42-7.31 (m, 2H) 33 δ = 8.76-8.75 (dd, 1H), 8.41 (t, 1H),8.34-8.32 (m, 1H), 622.23 622.22 8.29-8.21 (m, 5H), 7.92-7.83 (m, 5H),7.76-7.62 (m, 4H), 7.57-7.47 (m, 6H), 7.43-7.39 (m, 1H), 7.34-7.28 (m,2H) 52 δ = 8.77-8.75 (m, 1H), 8.50-8.48 (m, 1H), 8.39-8.37 (m, 507.18507.17 1H), 8.31-8.29 (m, 1H), 8.25-8.23 (dd, 1H), 8.11-8.09 (m, 1H),8.00-7.82 (m, 4H), 7.76-7.73 (m, 3H), 7.68-7.65 (m, 1H), 7.57-7.54 (m,3H), 7.49-7.41 (m, 3H), 7.10-7.06 (m, 1H) 63 δ = 9.68 (s, 1H), 8.90-8.88(m, 1H), 8.84-8.82 (m, 1H), 483.18 483.17 8.61-8.58 (m, 3H), 8.40-8.38(m, 1H), 8.32-8.30 (m, 1H), 8.17-8.12 (m, 3H), 7.94-7.88 (m, 2H),7.84-7.81 (m, 2H), 7.74-7.70 (m, 1H), 7.66-7.52 (m, 3H), 7.39-7.36 (m,1H), 7.15-7.12 (m, 1H) 70 δ = 8.81-8.79 (dd, 1H), 8.70-8.68 (m, 2H),8.50-8.48 (m, 533.20 533.19 1H), 8.432-8.30 (m, 1H), 8.26-8.23 (m, 3H),8.04-8.01 (m, 3H), 7.94-7.90 (m, 1H), 7.84-7.74 (m, 2H), 7.71-7.66 (m,3H), 7.57-7.53 (m, 1H), 7.49-7.46 (m, 1H), 7.42-7.37 (m, 2H), 7.27-7.23(m, 2H) 84 δ = 8.78-8.76 (dd, 1H), 8.50-8.45 (m, 3H), 8.42-8.40 (m,556.18 556.17 1H), 8.23-8.21 (m, 1H), 7.96-7.89 (m, 3H), 7.84-7.82 (m,1H), 7.76-7.68 (m, 6H), 7.65-7.59 (m, 3H), 7.52-7.40 (m, 7H) 91 δ =8.76-8.73 (m, 3H), 8.66-8.64 (m, 2H), 8.48-8.45 (m, 586.21 586.22 3H),8.45-8.43 (m, 1H), 8.30-8.24 (m, 3H), 8.07-8.04 (m, 5H), 7.95-7.87 (m,4H), 7.66-7.60 (m, 3H), 7.50-7.46 (m, 2H), 7.32-7.29 (m, 1H) 106 δ =8.79-8.77 (dd, 2H), 8.59-8.57 (m, 1H), 8.44-8.42 (m, 710.24 710.25 1H),8.40 (t, 1H), 8.37-8.35 (m, 1H), 8.32-8.30 (m, 1H), 8.28-8.26 (m, 1H),8.23-8.20 (m, 3H), 8.12-8.10 (m, 1H), 7.95-7.82 (m, 7H), 7.76-7.71 (m,4H), 7.66-7.53 (m, 4H), 7.49-7.44 (m, 3H) 125 δ = 8.80-8.78 (dd, 1H),8.59-8.57 (m, 1H), 8.43-8.40 (m, 633.21 633.22 2H), 8.23-8.20 (m, 2H),7.95-7.90 (m, 2H), 7.87-7.81 (m, 5H), 7.79-7.72 (m, 4H), 7.68-7.58 (m,5H), 7.49-7.46 (m, 1H), 7.39-7.30 (m, 4H)

Example 1

A Corning 15 Ohms per square centimeter (Ω/cm², 1,200 Å) ITO glasssubstrate was cut to a size of 50 millimeters (mm)×50 mm×0.7 mm, andthen, sonicated by using isopropyl alcohol and pure water, for 5 minutesrespectively, and cleaned by exposure to ultraviolet rays with ozone soas to use the glass substrate as an anode, and then, the glass substratewas mounted on a vacuum-deposition apparatus.

2-TNATA was vacuum-deposited on the glass substrate to form a holeinjection layer having a thickness of about 600 Å. Thereafter,4,4′-bis[N-(1-naphthyl)-N-phenylamino]biphenyl (a hole transportmaterial, hereinafter referred to as “NPB”) was vacuum-deposited on thehole injection layer to form a hole transport layer having a thicknessof about 300 Å.

9,10-di-naphthalene-2-yl-anthracene (hereinafter referred to as “ADN”)as a blue fluorescent host and4,4′-bis[2-(4-(N,N-diphenylamino)phenyl)vinyl]biphenyl (hereinafterreferred to as “DPAVBi”) as a blue fluorescent dopant were co-depositedon the hole transport layer in a weight ratio of about 98:2 to form anemission layer having a thickness of about 300 Å.

Afterward, Compound 2 was deposited on the emission layer to form anelectron transport layer having a thickness of about 300 Å. Then, LiF,an alkali metal halide, was deposited on the electron transport layer toform an electron injection layer having a thickness of about 10 Å.Aluminum (Al) was vacuum-deposited on the electron injection layer toform a cathode having a thickness of about 3,000 Å, thereby forming aLiF/Al electrode to complete the manufacture of an organiclight-emitting device.

Example 2

An organic light-emitting device was manufactured in the same (orsubstantially the same) manner as in Example 1, except that Compound 15was used instead of Compound 2 in the formation of an electron transportlayer.

Example 3

An organic light-emitting device was manufactured in the same (orsubstantially the same) manner as in Example 1, except that Compound 33was used instead of Compound 2 in the formation of an electron transportlayer.

Example 4

An organic light-emitting device was manufactured in the same (orsubstantially the same) manner as in Example 1, except that Compound 84was used instead of Compound 2 in the formation of an electron transportlayer.

Example 5

An organic light-emitting device was manufactured in the same (orsubstantially the same) manner as in Example 1, except that Compound 106was used instead of Compound 2 in the formation of an electron transportlayer.

Example 6

An organic light-emitting device was manufactured in the same (orsubstantially the same) manner as in Example 1, except that Compound 125was used instead of Compound 2 in the formation of an electron transportlayer.

Comparative Example 1

An organic light-emitting device was manufactured in the same (orsubstantially the same) manner as in Example 1, except that Alq₃ wasused instead of Compound 2 in the formation of an electron transportlayer. The organic light-emitting device exhibited blue emission of adriving voltage of about 7.35 V, an emission luminance of about 2,065cd/m², and a current efficiency of about 4.13 cd/A at a current densityof about 50 mA/cm². The half-lifespan of luminance of the organiclight-emitting device was about 145 hours at a current density of about100 mA/cm².

The results of measuring the driving voltage (V), current density(mA/cm₂), luminance (cd/m²), efficiency (cd/A), emission color, andhalf-lifespan of the organic light-emitting devices manufactured inExamples 1 to 6 and Comparative Example 1 are shown in Table 2.

TABLE 1 Electron Driving Current Half lifespan transport voltage densityLuminance Efficiency Emission (hr @ layer (V) (mA/cm²) (cd/m²) (cd/A)color 100 mA/cm²) Example 1 Compound 2 5.72 50 3,325 6.65 blue 231 hoursExample 2 Compound 15 6.02 50 3,040 6.08 blue 376 hours Example 3Compound 33 5.97 50 3,210 6.42 blue 335 hours Example 4 Compound 84 5.9150 3,110 6.22 blue 359 hours Example 5 Compound 106 5.63 50 3,215 6.43blue 314 hours Example 6 Compound 125 5.55 50 3,190 6.38 blue 321 hoursComparative Alq₃ 7.35 50 2,065 4.13 blue 145 hours Example 1

As can be seen from the results shown in Table 2, when the compoundrepresented by Formula 1 was used as an electron transport material,driving voltages of the organic light-emitting devices manufactured inExamples 1 to 6 were lower than that of Comparative Example 1 by atleast 1 V. Furthermore, the organic light-emitting devices manufacturedin Examples 1 to 6 exhibited excellent I-V-L (current-voltage-luminance)characteristics with significant improvement of efficiency and lifespan.Accordingly, it can be seen that the compound represented by Formula 1according to an example embodiment of the present disclosure may beappropriate for use as an electron transport material.

An organic light-emitting device according to embodiments of the presentdisclosure may have high efficiency, low voltage, high luminance, and along lifespan.

As used herein, the terms “use,” “using,” and “used” may be consideredsynonymous with the terms “utilize,” “utilizing,” and “utilized,”respectively.

In addition, the terms “substantially,” “about,” and similar terms areused as terms of approximation and not as terms of degree, and areintended to account for the inherent deviations in measured orcalculated values that would be recognized by those of ordinary skill inthe art.

Also, any numerical range recited herein is intended to include allsubranges of the same numerical precision subsumed within the recitedrange. For example, a range of “1.0 to 10.0” is intended to include allsubranges between (and including) the recited minimum value of 1.0 andthe recited maximum value of 10.0, that is, having a minimum value equalto or greater than 1.0 and a maximum value equal to or less than 10.0,such as, for example, 2.4 to 7.6. Any maximum numerical limitationrecited herein is intended to include all lower numerical limitationssubsumed therein and any minimum numerical limitation recited in thisspecification is intended to include all higher numerical limitationssubsumed therein. Accordingly, Applicant reserves the right to amendthis specification, including the claims, to expressly recite anysub-range subsumed within the ranges expressly recited herein.

It should be understood that example embodiments described herein shouldbe considered in a descriptive sense only and not for purposes oflimitation. Descriptions of features or aspects within each exampleembodiment should typically be considered as available for other similarfeatures or aspects in other example embodiments.

While one or more example embodiments have been described with referenceto the drawing, it will be understood by those of ordinary skill in theart that various changes in form and details may be made therein withoutdeparting from the spirit and scope of the present disclosure as definedby the following claims and equivalents thereof.

What is claimed is:
 1. A compound represented by Formula 1:

wherein, in Formula 1, A₁ to A₈ are each independently selected fromCR₁₁, CR₁₂, CR₁₃, CR₁₄, CR₁₅, CR₁₆, CR₁₇, CR₁₈, and N, wherein at leastone selected from A₁ to A₈ is N; R₁ is selected from deuterium, ahalogen group, a nitro group, a cyano group, a substituted orunsubstituted C₁-C₆₀ alkyl group, a substituted or unsubstituted C₂-C₆₀alkenyl group, a substituted or unsubstituted C₂-C₆₀ alkynyl group, asubstituted or unsubstituted C₁-C₆₀ alkoxy group, a substituted orunsubstituted C₃-C₁₀ cycloalkyl group, a substituted or unsubstitutedC₂-C₁₀ heterocycloalkyl group, a substituted or unsubstituted C₃-C₁₀cycloalkenyl group, a substituted or unsubstituted C₂-C₁₀heterocycloalkenyl group, a substituted or unsubstituted C₆-C₆₀ arylgroup, a substituted or unsubstituted C₆-C₆₀ aryloxy group, asubstituted or unsubstituted C₆-C₆₀ arylthio group, a substituted orunsubstituted C₁-C₆₀ heteroaryl group, a substituted or unsubstitutedmonovalent non-aromatic condensed polycyclic group, a substituted orunsubstituted monovalent non-aromatic condensed heteropolycyclic group,P(═O)R₃₁R₃₂, P(═S)R₃₃R₃₄, S(═O)₂R₃₅, and S(═O)R₃₆; R₂ is selected fromhydrogen, deuterium, a halogen group, a nitro group, a cyano group, asubstituted or unsubstituted C₁-C₆₀ alkyl group, a substituted orunsubstituted C₂-C₆₀ alkenyl group, a substituted or unsubstitutedC₂-C₆₀ alkynyl group, a substituted or unsubstituted C₁-C₆₀ alkoxygroup, a substituted or unsubstituted C₃-C₁₀ cycloalkyl group, asubstituted or unsubstituted C₂-C₁₀ heterocycloalkyl group, asubstituted or unsubstituted C₃-C₁₀ cycloalkenyl group, a substituted orunsubstituted C₂-C₁₀ heterocycloalkenyl group, a substituted orunsubstituted C₆-C₆₀ aryl group, a substituted or unsubstituted C₆-C₆₀aryloxy group, a substituted or unsubstituted C₆-C₆₀ arylthio group, asubstituted or unsubstituted C₁-C₆₀ heteroaryl group, a substituted orunsubstituted monovalent non-aromatic condensed polycyclic group, asubstituted or unsubstituted monovalent non-aromatic condensedheteropolycyclic group, P(═O)R₃₁R₃₂, P(═S)R₃₃R₃₄, S(═O)₂R₃₅, andS(═O)R₃₆; R₁₁, R₁₂, R₁₃, R₁₄, R₁₅, R₁₆, R₁₇, and R₁₈ are eachindependently hydrogen; R₃₁, R₃₂, R₃₃, R₃₄, R₃₅, and R₃₆ are eachindependently selected from hydrogen, deuterium, a halogen group, anitro group, a cyano group, a substituted or unsubstituted C₁-C₆₀ alkylgroup, a substituted or unsubstituted C₆-C₆₀ aryl group, a substitutedor unsubstituted C₁-C₆₀ heteroaryl group, and a substituted orunsubstituted monovalent non-aromatic condensed polycyclic group; L₁ andL₂ are each independently selected from a substituted or unsubstitutedC₆-C₆₀ arylene group, a substituted or unsubstituted C₁-C₆₀heteroarylene group, a substituted or unsubstituted divalentnon-aromatic condensed polycyclic group, and a substituted orunsubstituted divalent non-aromatic condensed heteropolycyclic group; a1and a2 are each independently an integer from 0 to 3; m and n are eachindependently an integer selected from 1 to 2; and at least onesubstituent of the substituted C₁-C₆₀ alkyl group, substituted C₂-C₆₀alkenyl group, substituted C₂-C₆₀ alkynyl group, substituted C₁-C₆₀alkoxy group, substituted C₃-C₁₀ cycloalkyl group, substituted C₂-C₁₀heterocycloalkyl group, substituted C₃-C₁₀ cycloalkenyl group,substituted C₂-C₁₀ heterocycloalkenyl group, substituted C₆-C₆₀ arylgroup, substituted C₆-C₆₀ aryloxy group, substituted C₆-C₆₀ arylthiogroup, substituted C₁-C₆₀ heteroaryl group, substituted monovalentnon-aromatic condensed polycyclic group, substituted monovalentnon-aromatic condensed heteropolycyclic group, substituted C₆-C₆₀arylene group, substituted C₁-C₆₀ heteroarylene group, a substituteddivalent non-aromatic condensed polycyclic group, and a substituteddivalent non-aromatic condensed heteropolycyclic group is selected fromthe group consisting of: deuterium, —F, —Cl, —Br, —I, a hydroxyl group,a cyano group, a nitro group, an amino group, an amidino group, ahydrazine group, a hydrazone group, a carboxylic acid group or a saltthereof, a sulfonic acid group or a salt thereof, a phosphoric acidgroup or a salt thereof, a C₁-C₆₀ alkyl group, a C₂-C₆₀ alkenyl group, aC₂-C₆₀ alkynyl group, and a C₁-C₆₀ alkoxy group, a C₁-C₆₀ alkyl group, aC₂-C₆₀ alkenyl group, a C₂-C₆₀ alkynyl group, and a C₁-C₆₀ alkoxy group,each substituted with at least one selected from deuterium, —F, —Cl,—Br, —I, a hydroxyl group, a cyano group, a nitro group, an amino group,an amidino group, a hydrazine group, a hydrazone group, a carboxylicacid group or a salt thereof, a sulfonic acid group or a salt thereof, aphosphoric acid group or a salt thereof, a C₃-C₁₀ cycloalkyl group, aC₂-C₁₀ heterocycloalkyl group, a C₃-C₁₀ cycloalkenyl group, a C₂-C₁₀heterocycloalkenyl group, a C₆-C₆₀ aryl group, a C₆-C₆₀ aryloxy group, aC₆-C₆₀ arylthio group, a C₁-C₆₀ heteroaryl group, a monovalentnon-aromatic condensed polycyclic group, a monovalent non-aromaticcondensed heteropolycyclic group, —N(Q₁₁)(Q₁₂), —Si(Q₁₃)(Q₁₄)(Q₁₅), and—B(Q₁₆)(Q₁₇), a C₃-C₁₀ cycloalkyl group, a C₂-C₁₀ heterocycloalkylgroup, a C₃-C₁₀ cycloalkenyl group, a C₂-C₁₀ heterocycloalkenyl group, aC₆-C₆₀ aryl group, a C₆-C₆₀ aryloxy group, a C₆-C₆₀ arylthio group, aC₁-C₆₀ heteroaryl group, a monovalent non-aromatic condensed polycyclicgroup, and a monovalent non-aromatic condensed heteropolycyclic group,and a C₃-C₁₀ cycloalkyl group, a C₂-C₁₀ heterocycloalkyl group, a C₃-C₁₀cycloalkenyl group, a C₂-C₁₀ heterocycloalkenyl group, a C₆-C₆₀ arylgroup, a C₆-C₆₀ aryloxy group, a C₆-C₆₀ arylthio group, a C₁-C₆₀heteroaryl group, a monovalent non-aromatic condensed polycyclic group,and a monovalent non-aromatic condensed heteropolycyclic group, eachsubstituted with at least one selected from deuterium, —F, —Cl, —Br, —I,a hydroxyl group, a cyano group, a nitro group, an amino group, anamidino group, a hydrazine group, a hydrazone group, a carboxylic acidgroup or a salt thereof, a sulfonic acid group or a salt thereof, aphosphoric acid group or a salt thereof, a C₁-C₆₀ alkyl group, a C₂-C₆₀alkenyl group, a C₂-C₆₀ alkynyl group, a C₁-C₆₀ alkoxy group, a C₃-C₁₀cycloalkyl group, a C₂-C₁₀ heterocycloalkyl group, a C₃-C₁₀ cycloalkenylgroup, a C₂-C₁₀ heterocycloalkenyl group, a C₆-C₆₀ aryl group, a C₆-C₆₀aryloxy group, a C₆-C₆₀ arylthio group, a C₁-C₆₀ heteroaryl group, amonovalent non-aromatic condensed polycyclic group, a monovalentnon-aromatic condensed heteropolycyclic group, —N(Q₂₁)(Q₂₂),—Si(Q₂₃)(Q₂₄)(Q₂₅), and —B(Q₂₆)(Q₂₇), wherein Q₁₁ to Q₁₇ and Q₂₁ to Q₂₇are each independently selected from hydrogen, deuterium, —F, —Cl, —Br,—I, a hydroxyl group, a cyano group, a nitro group, an amino group, anamidino group, a hydrazine group, a hydrazone group, a carboxylic acidgroup or a salt thereof, a sulfonic acid group or a salt thereof, aphosphoric acid group or a salt thereof, a C₁-C₆₀ alkyl group, a C₂-C₆₀alkenyl group, a C₂-C₆₀ alkynyl group, a C₁-C₆₀ alkoxy group, a C₃-C₁₀cycloalkyl group, a C₂-C₁₀ heterocycloalkyl group, a C₃-C₁₀ cycloalkenylgroup, a C₂-C₁₀ heterocycloalkenyl group, a C₆-C₆₀ aryl group, a C₁-C₆₀heteroaryl group, a monovalent non-aromatic condensed polycyclic group,and a monovalent non-aromatic condensed heteropolycyclic group.
 2. Thecompound of claim 1, wherein R₃₁, R₃₂, R₃₃, R₃₄, R₃₅, and R₃₆ in Formula1 are each independently a substituted or unsubstituted C₆-C₆₀ arylgroup.
 3. The compound of claim 1, wherein L₁ and L₂ in Formula 1 areeach independently one of Formulae 2a to 2d:

wherein “*” in Formulae 2a to 2d indicates a binding site.
 4. Thecompound of claim 1, wherein R₁ in Formula 1 is selected from deuterium,a cyano group, P(═O)R₃₁R₃₂, P(═S)R₃₃R₃₄, and a group represented by oneof Formulae 3a to 3k; and R₂ in Formula 1 is selected from hydrogen,deuterium, a cyano group, P(═O)R₃₁R₃₂, P(═S)R₃₃R₃₄, and a grouprepresented by one of Formulae 3a to 3k:

wherein in Formulae 3a to 3k, H₁ is selected from CR₄₁R₄₂, NR₄₃, O, andS; R₄₁ to R₄₃, Z₁, and Z₂ are each independently selected from hydrogen,deuterium, a halogen group, a cyano group, a nitro group, a hydroxylgroup, a carboxy group, a substituted or unsubstituted C₁ to C₂₀ alkylgroup, a substituted or unsubstituted C₆ to C₂₀ aryl group, asubstituted or unsubstituted C₁ to C₂₀ heteroaryl group, a substitutedor unsubstituted monovalent non-aromatic condensed polycyclic group, anda substituted or unsubstituted monovalent non-aromatic condensedheteropolycyclic group; p in Formulae 3a and 3k is an integer selectedfrom 1 to 4, p in Formula 3c is an integer selected from 1 to 3, p inFormula 3d is an integer selected from 1 to 9, p in Formulae 3e and 3gis an integer selected from 1 to 6, p in Formula 3f is an integerselected from 1 to 5, and p in Formulae 3h, 3i, and 3j is an integerselected from 1 to 7, wherein when p is 2 or more, two or more Z₁(s) areidentical to or different from each other; and * indicates a bindingsite.
 5. The compound of claim 1, wherein the compound of Formula 1 isrepresented by Formula 2:


6. The compound of claim 1, wherein the compound of Formula 1 isrepresented by Formula 3:


7. The compound of claim 1, wherein the compound of Formula 1 isrepresented by Formula 4:


8. The compound of claim 1, wherein the compound of Formula 1 isrepresented by Formula 5:


9. A compound represented by one of Compounds 1 to 113 and 124 to 127:


10. An organic light-emitting device comprising: a first electrode; asecond electrode facing the first electrode; and an organic layerbetween the first electrode and the second electrode, the organic layercomprising an emission layer, wherein the organic layer comprises thecompound of claim
 1. 11. The organic light-emitting device of claim 10,wherein the first electrode is an anode, the second electrode is acathode, and the organic layer comprises: i) a hole transport regionbetween the first electrode and the emission layer, the hole transportregion comprising at least one selected from a hole transport layer, ahole injection layer, and an electron blocking layer, and ii) anelectron transport region between the emission layer and the secondelectrode, the electron transport region comprising an electrontransport layer and at least one selected from a hole blocking layer andan electron injection layer.
 12. The organic light-emitting device ofclaim 11, wherein the electron transport region comprises the compoundrepresented by Formula
 1. 13. The organic light-emitting device of claim11, wherein the electron transport layer comprises the compoundrepresented by Formula
 1. 14. The organic light-emitting device of claim11, wherein the hole transport region comprises a charge-generatingmaterial.
 15. The organic light-emitting device of claim 14, wherein thecharge-generating material is a p-dopant.
 16. The organic light-emittingdevice of claim 14, wherein the charge-generating material is HT-D1 orF4-TCNQ:


17. The organic light-emitting device of claim 11, wherein the electrontransport region comprises a metal-containing material.
 18. The organiclight-emitting device of claim 11, wherein the electron transport regioncomprises ET-D1 or ET-D2:


19. A display apparatus comprising the organic light-emitting device ofclaim 10, wherein the first electrode of the organic light-emittingdevice is electrically coupled to a source electrode or a drainelectrode of a thin film transistor.